CN113178538A

CN113178538A - Organic electroluminescent element, display device, lighting device, and anthracene compound

Info

Publication number: CN113178538A
Application number: CN202110100959.2A
Authority: CN
Inventors: 畠山琢次; 藤田幸宏; 王国防; 田岛晶夫; 森绚子; 水谷彰英; 川角亮介; 久田梨香
Original assignee: Kansai College; SK Materials JNC Co Ltd
Current assignee: Kansai College; SK Materials JNC Co Ltd
Priority date: 2020-01-27
Filing date: 2021-01-25
Publication date: 2021-07-27

Abstract

The present invention relates to an organic electroluminescent element, a display device, a lighting device, and an anthracene compound, including a pair of electrodes including an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer including an anthracene compound represented by formula (1) below as a host material, and a polycyclic aromatic compound represented by formula (2) below or a multimer thereof as a dopant material (Ar in formula (1), Ar in formula (1))^cIs aryl or the like, R^cIs hydrogen, etc., Ar¹¹～Ar¹⁸Any two of which are aryl or the like and the others are hydrogen or the like, at least one hydrogen in the formula (1) may be substituted by deuterium or the like, in the formula (2), the A ring, the B ring and the C ring are aryl rings which may be substituted or the like, and X is¹And X²Is > O, > N-R (R is aryl, etc.).

Description

Organic electroluminescent element, display device, lighting device, and anthracene compound

Technical Field

The present invention relates to an organic electroluminescent element, and a display device and a lighting device using the same. In addition, the present invention relates to an anthracene compound useful as a light-emitting material.

Background

Conventionally, display devices using light-emitting elements that perform Electroluminescence have been studied in various ways because they can achieve power saving and reduction in thickness, and further, organic Electroluminescence (hereinafter, sometimes referred to as "organic EL element") elements including organic materials have been studied actively because they are easy to reduce the weight and increase the size. In particular, the development of organic materials having light-emitting characteristics such as blue, which is one of the three primary colors of light, and the combination of a plurality of materials exhibiting optimum light-emitting characteristics have been actively studied so far, regardless of whether they are high-molecular compounds or low-molecular compounds.

The organic EL element has a structure including: a pair of electrodes including an anode and a cathode; and one or more layers which are disposed between the pair of electrodes and contain an organic compound. The layer containing an organic compound includes a light-emitting layer, a charge transporting/injecting layer for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

Patent document 1 describes the use of an anthracene compound as a light-emitting material of an organic electroluminescent element. In recent years, polycyclic aromatic compounds in which a plurality of aromatic rings are condensed with boron or the like as a central atom have been reported as materials for organic electroluminescent elements (patent document 2).

[ Prior art documents ]

[ patent document ]

[ patent document 1] International publication No. 2006/003842

[ patent document 2] International publication No. 2015/102118

Disclosure of Invention

[ problems to be solved by the invention ]

As described above, various materials have been developed as materials for organic EL devices, but in order to increase the options for materials for organic EL devices, it is desired to develop a material containing a compound different from conventional materials. The invention provides an organic EL element using a combination of new materials. The present invention addresses the problem of providing an organic EL element having high external quantum efficiency.

[ means for solving problems ]

The present inventors have made extensive studies to solve the above problems, and as a result, have found that an excellent organic EL element can be obtained by using 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, and have completed the present invention. That is, the present invention provides an organic electroluminescent element and an anthracene compound as described below.

< 1 > an organic electroluminescent element comprising a pair of electrodes including an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing an anthracene compound represented by the following formula (1) as a host material and a polymer 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,

[ solution 1]

In the formula (1), the reaction mixture is,

Ar^cis an optionally substituted aryl or an optionally substituted heteroaryl group,

R^cis hydrogen, alkyl or cycloalkyl,

Ar¹¹、Ar¹²、Ar¹³、Ar¹⁴、Ar¹⁵、Ar¹⁶、Ar¹⁷and Ar¹⁸Each independently is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino An alkyl group, a cycloalkyl group which may be substituted, an alkenyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, or a silyl group which may be substituted,

at least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

In the formula (2), the reaction mixture is,

ring A, ring B and ring C are each independently an aryl or heteroaryl ring, at least one hydrogen in these rings may be substituted,

X¹and X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, said > C (-R)₂R of (a) is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, and additionally, said R > N-R and/or said > C (-R)₂R of (A) may be bonded to the A ring, the B ring and/or the C ring through a linking group or a single bond,

at least one of an aryl ring and a heteroaryl ring in the compound represented by formula (2) or a multimer thereof may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH in the cycloalkane₂-may be substituted by-O-,

At least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or halogen.

< 2 > the organic electroluminescent element according to < 1 > wherein the polycyclic aromatic compound represented by formula (2) or the multimer of the polycyclic aromatic compound having a structure represented by a plurality of formulae (2) is a multimer of the polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or the polycyclic aromatic compound having a structure represented by a plurality of formulae (2-a), (2-b), (2-c), formula (2-d), formula (2-e) or formula (2-f),

[ solution 2]

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),

R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰and R¹¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹May be bonded to each other and together with the a-, b-or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the ring formed may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl group, at least one of which may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group,

X_XEach independently > O, > S, > N-R or > C (-R)₂R of said > N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and additionally said > C (-R)₂Each R of (A) is independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl,

X¹and X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is C6-12 aryl which may be substituted by C1-6 alkyl or C3-14 cycloalkyl, or C1-6 alkyl or C3-14 ringAn alkyl-substituted heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, wherein & gtC (-R)₂R in (b) is hydrogen, an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and R > N-R and/or C (-R)₂R of (a) can be represented by-O-, -S-, -C (-R)₂-or a single bond to the a-ring, b-ring and/or C-ring, the-C (-R)₂R is independently an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

At least one of an aryl ring and a heteroaryl ring in the compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or a multimer thereof may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH in the cycloalkane₂-may be substituted by-O-,

at least one hydrogen in the compound or structure represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) may be substituted with deuterium, cyano or halogen,

in the case of multimers, are dimers or trimers having two or three structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f).

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

< 4 > the organic electroluminescent element according to < 3 > wherein the compound represented by the formula (2) is any one of compounds represented by the following formulae,

[ solution 3]

[ solution 4]

[ solution 5]

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

< 5 > the organic electroluminescent element according to any one of < 1 > to < 4 >, wherein in formula (1),

Ar¹¹、Ar¹²、Ar¹³、Ar¹⁴、Ar¹⁵、Ar¹⁶、Ar¹⁷and Ar¹⁸Any two of which are aryl which may be substituted or heteroaryl which may be substituted, the other six of which are hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted or alkoxy which may be substituted.

< 6 > the organic electroluminescent element according to < 5 >, wherein the anthracene compound represented by the formula (1) is an anthracene compound represented by the following formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E),

[ solution 6]

In the formula (1A), the formula (1B), the formula (1C), the formula (1D) or the formula (1E),

Ar^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' and Ar¹⁸' independently of one another are phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, quaterphenyl, naphthyl,

A phenyl group, a triphenylene group, a pyrenyl group or a group represented by the formula (A), at least one hydrogen of these groups being represented by a phenyl group, a biphenyl group, a terphenyl group, a tetrakis-biphenyl groupPhenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, fluorenyl, or the like,

A phenyl group, a triphenylene group, a pyrenyl group or a group represented by the formula (A), wherein when both hydrogens of the methylene group in the fluorenyl group and the benzofluorenyl group are substituted with phenyl groups, the phenyl groups may be bonded to each other by a single bond,

In the absence of a bond Ar^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' or Ar¹⁸Instead of hydrogen, the anthracene ring of' may have a methyl or tert-butyl group bonded to a carbon atom,

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

the group represented by formula (A) is a group obtained by removing one hydrogen at any position of formula (A), and represents the position,

in the formula (A), Y is-O-, -S-or > N-R³⁹，R²¹～R²⁸Each independently hydrogen, alkyl which may be substituted, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R²¹～R²⁸Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted by an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group, R ³⁹Is hydrogen or a substituted aryl group.

< 7 > the organic electroluminescent element according to < 6 >, wherein

The group represented by the formula (A) is a group represented by any one of the formulae (A-1) to (A-14),

the group represented by the formula (A-1) to the formula (A-14) is a group obtained by removing one hydrogen at any position of each of the formula (A-1) to the formula (A-14),

in the formulae (A-1) to (A-14), Y is-O-, -S-or > N-R³⁹，R³⁹At least one hydrogen of the groups represented by the formulae (A-1) to (A-14) may be substituted by an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, a diaryl-substituted amino group, a diheteroaryl-substituted amino group, an arylheteroaryl-substituted amino group, a halogen, a hydroxyl group or a cyano group, for hydrogen or an aryl group.

[ solution 7]

< 8 > the organic electroluminescent element according to < 6 > or < 7 >, wherein

Ar^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' and Ar¹⁸' are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of formulae (A-1) to (A-4), at least one hydrogen of these groups being substituted by a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of formulae (A-1) to (A-4),

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

< 9 > the organic electroluminescent element according to < 5 > wherein Ar¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸Are all hydrogen.

< 10 > the organic electroluminescent element according to < 9 > wherein Ar is selected from the group consisting of^c、Ar¹⁴And Ar¹⁵At least one of the group consisting is an anthracycline-containing radical.

< 11 > the organic electroluminescent element according to < 9 > wherein Ar is selected from the group consisting of^c、Ar¹⁴And Ar¹⁵At least one of the group consisting of a group represented by the formula (A'),

[ solution 8]

In the formula (A'), R²¹～R²⁸Each independently hydrogen, alkyl which may be substituted, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R²¹～R²⁸Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted by an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group.

< 12 > the organic electroluminescent element according to < 9 > wherein at least one hydrogen in the compound represented by formula (1) may be substituted with deuterium.

< 13 > the organic electroluminescent element according to any one of < 1 > to < 12 > having an electron transport layer and/or an electron injection layer disposed between the cathode and the light-emitting layer, at least one of the electron transport layer and the electron injection layer containing at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and oxazoline derivatives (azoline).

< 14 > the organic electroluminescent element according to < 13 >, wherein the electron transport layer and/or the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals.

< 15 > a display device comprising the organic electroluminescent element according to any one of < 1 > to < 14 >.

< 16 > a lighting device comprising the organic electroluminescent element according to any one of < 1 > to < 14 >.

< 17 > an anthracene compound represented by the following formula (1):

[ solution 9]

In the formula (1), the reaction mixture is,

R^cis hydrogen, alkyl or cycloalkyl,

Ar¹¹、Ar¹²、Ar¹³、Ar¹⁴、Ar¹⁵、Ar¹⁶、Ar¹⁷and Ar¹⁸Each independently is hydrogen, optionally substituted aryl, optionally substitutedHeteroaryl, 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, alkenyl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, or silyl which may be substituted,

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

[ solution 10]

In the formula (1Aa), Ar^c'、Ar¹⁴' and Ar¹⁵' are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, or,

A phenyl group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulae (A-1) to (A-14), wherein at least one hydrogen in the groups may be selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a fluorenyl group, a,

A phenyl group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulae (A-1) to (A-14), wherein when hydrogen of a methylene group in the fluorenyl group and the benzofluorenyl group is substituted with a phenyl group, the phenyl groups may be bonded to each other by a single bond, and Ar is not bonded thereto^c'、Ar¹⁴' or Ar¹⁵Instead of hydrogen, the anthracene ring of' may have a methyl or tert-butyl group bonded to a carbon atom,

at least one hydrogen in the compound represented by formula (1Aa) may be substituted with halogen, cyano or deuterium,

in the formulae (A-1) to (A-14), Y is-O-, -S-or > N-R³⁹，R³⁹At least one hydrogen of the groups represented by the formulae (A-1) to (A-14) may be substituted by an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, a diaryl-substituted amino group, a diheteroaryl-substituted amino group, an arylheteroaryl-substituted amino group, a halogen, a hydroxyl group or a cyano group, and may be hydrogen or an aryl group,

Wherein at least one hydrogen in the compound represented by formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (1Aa) may be substituted with deuterium.

< 19 > the anthracene compound according to < 18 >, wherein Ar^c'、Ar¹⁴' and Ar¹⁵' are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of formulae (A-1) to (A-4), and at least one hydrogen of these groups may be substituted by a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of formulae (A-1) to (A-4).

< 20 > the anthracene compound according to < 18 > or < 19 >, wherein in formula (1Aa), at least hydrogen bonded to the 10-position of the anthracene ring is substituted with deuterium.

< 21 > the anthracene compound according to < 18 > represented by any of the following formulae:

[ solution 11]

[ solution 12]

[ solution 13]

[ solution 14]

(in the formula, D represents deuterium).

< 22 > the anthracene compound according to < 17 > represented by any of the following formulae:

[ solution 15]

[ solution 16]

[ solution 17]

[ solution 18]

[ solution 19]

[ solution 20]

[ solution 21]

(in the formula, D represents deuterium).

< 23 > the anthracene compound according to < 17 > represented by any of the following formulae:

[ solution 22]

[ solution 23]

[ solution 24]

[ solution 25]

< 24 > the anthracene compound according to < 17 > represented by any of the following formulae:

[ solution 26]

[ solution 27]

[ solution 28]

[ solution 29]

(in the formula, D represents deuterium).

< 25 > the anthracene compound according to < 17 > represented by any of the following formulae:

[ solution 30]

[ solution 31]

(in the formula, D represents deuterium).

< 26 > the anthracene compound according to < 17 > represented by any of the following formulae:

[ solution 32]

(in the formula, Me represents a methyl group, tBu represents a tert-butyl group, and CyHex represents a cyclohexyl group).

< 27 > the anthracene compound according to < 17 > represented by any of the following formulae:

[ solution 33]

[ chemical 34]

(in the formula, D represents deuterium).

[ Effect of the invention ]

The present invention can provide an organic EL element using a combination of new materials. The organic EL element of the present invention has high external quantum efficiency and can emit light at a low voltage. Further, according to the present invention, an anthracene compound which can be used for producing the organic EL device can be provided.

Drawings

Fig. 1 is a schematic cross-sectional view showing an example of an organic EL device of the present invention.

[ description of symbols ]

100: organic electroluminescent element

101: substrate

102: anode

103: hole injection layer

104: hole transport layer

105: luminescent layer

106: electron transport layer

107: electron injection layer

108: cathode electrode

Detailed Description

The present invention will be described in detail below. The following description of the constituent elements may be based on a representative embodiment or a specific example, but the present invention is not limited to such an embodiment. In the present specification, the numerical range expressed by the term "to" means a range including the numerical values described before and after the term "to" as the lower limit value and the upper limit value. In the present specification, "hydrogen" in the description of the structural formulae means "hydrogen atom (H)".

In the present specification, the chemical structure or the substituent may be represented by carbon number, but the carbon number when the substituent is substituted in the chemical structure or when the substituent is substituted on the substituent or the like means the carbon number of each of the chemical structure or the substituent, 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, the phrase "substituent B having a carbon number Y substituted with a substituent a having a carbon number X" means that "substituent a having a carbon number X" is substituted with "substituent B having a carbon number Y", and the carbon number Y is not the total carbon number of substituent a and substituent B. For example, the phrase "substituent B having a carbon number Y substituted with a substituent a" means that the substituent a "(not limited to a carbon number) is substituted with the" substituent B having a carbon number Y ", and the carbon number Y is not the total carbon number of the substituent a and the substituent B.

Organic electroluminescent element

The organic electroluminescent element of the present invention includes: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes. Fig. 1 is a schematic cross-sectional view showing an example of an organic EL device of the present invention.

The organic EL element 100 shown in fig. 1 includes: the light-emitting device comprises a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

In addition, the organic EL device 100 may be formed by reversing the manufacturing order, for example, by a structure including: the organic light emitting diode comprises a substrate 101, a cathode 108 arranged on the substrate 101, an electron injection layer 107 arranged on the cathode 108, an electron transport layer 106 arranged on the electron injection layer 107, a light emitting layer 105 arranged on the electron transport layer 106, a hole transport layer 104 arranged on the light emitting layer 105, a hole injection layer 103 arranged on the hole transport layer 104, and an anode 102 arranged on the hole injection layer 103.

The above layers are not all necessary, and the minimum structural unit is a structure including 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 layer 107 are arbitrarily provided. In addition, each of the layers may include a single layer, or may include a plurality of layers.

The form of the layer constituting the organic EL element may be, in addition to the structural form of "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode"), The structural forms of "substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode", "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/light-emitting layer/electron injection layer/cathode".

1. Light-emitting layer of organic electroluminescent element

The light-emitting layer 105 emits light by recombination of holes injected from the anode 102 and 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) which emits light when excited by recombination of holes and electrons, and is preferably a compound which can be formed into a stable thin film shape and which exhibits strong light emission (fluorescence) efficiency in a solid state.

As the light emission mechanism of the organic EL element, there are mainly two types of light emission, i.e., fluorescence light emission using light emission from an excited singlet state and phosphorescence light emission using light emission from an excited triplet state. The exciton utilization efficiency of a general fluorescent light-emitting material is low, and the maximum exciton utilization efficiency is 25%. However, using the phenomenon of generating singlet excitons from a plurality of Triplet excitons (Triplet-Triplet Fusion), it is possible to use 40% to 62.5% of the energy for light emission at the maximum.

There are two cases of generating singlet excitons from triplet excitons: on host material molecules, and on dopant material molecules. The triplet energy level of the dopant material at this time is preferably higher than the triplet energy level of the host material. If the relation of the triplet energy levels is satisfied, triplet excitons generated on the host material are not transferred to the dopant material having a higher triplet energy. In addition, triplet excitons generated on the dopant material molecules rapidly transfer energy to the host material molecules. That is, triplet excitons of the host material are not transferred to the dopant material, and the triplet excitons efficiently collide with each other on the host material, thereby generating singlet excitons. Further, when the singlet level of the dopant material is lower than the singlet level of the host material, singlet excitons generated by the TTF phenomenon rapidly transfer energy from the host material to the dopant material, contributing to fluorescent emission of the dopant material. In this case, the energy transfer from the host to the dopant is a fisherter (Foerster) type energy transfer. In general, it is known that in an organic EL element, the overlap integral between the fluorescence spectrum of a host and the absorption spectrum of a dopant is large, and that when the host and the dopant are close to each other and an appropriate orientation is obtained, efficient fisher-type energy transfer occurs.

When the host material which is the anthracene compound represented by the formula (1) and the dopant material which is the polycyclic aromatic compound having boron represented by the formula (2) are used, materials and devices which satisfy the above-described conditions for causing the appropriate energy level relationship between the host and the dopant and the efficient fisher-type energy transfer can be designed. As a result, the TTF phenomenon can be efficiently generated in the light-emitting layer of the present invention, and favorable element characteristics can be provided.

The light-emitting layer of the organic electroluminescent element of the present invention contains an anthracene compound represented by formula (1) as a host material, and a polycyclic aromatic compound represented by formula (2) or a polymer of polycyclic aromatic compounds having a plurality of structures represented by formula (2) as a dopant material.

1-1-1. anthracene series compound

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

[ solution 35]

In the formula (1), Ar^cIs optionally substituted aryl or optionally substituted heteroaryl, R^cIs hydrogen, alkyl or cycloalkyl, Ar¹¹、Ar¹²、Ar¹³、Ar¹⁴、Ar¹⁵、Ar¹⁶、Ar¹⁷And Ar¹⁸Each independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, 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, alkenyl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, or silyl which may be substituted, at least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium.

Examples of the "aryl group" of the "aryl group which may be substituted" in the formula (1) include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 16 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups having 6 to 10 carbon atoms.

Specific "aryl" groups include: phenyl as a monocyclic system; biphenyl as a bicyclic ring system; naphthyl as the condensed bicyclic system; terphenyl (m-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic system; anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl as condensed tricyclic systems; triphenylene, pyrenyl, tetracenyl, benzofluorenyl as condensed quaternary ring systems; perylene groups and pentacene groups as condensed five-ring systems, and the like. Further, in the present specification, when referring to "fluorenyl group", it means that one or both of two hydrogens of the fluorenyl group or a methylene group of the fluorenyl group are substituted with a methyl group. In addition, when referring to "benzofluorenyl", it means that one or both of the two hydrogens of the benzofluorenyl group or the methylene group of the benzofluorenyl group is substituted with a methyl group.

Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" in the formula (1) include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, still more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Specific examples of the "heteroaryl group" include: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzo [ b ] thienyl, dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naphthobenzofuryl, naphthobenzothienyl, and the like.

As the aryl and heteroaryl groups in each of the "diarylamino group which may be substituted", "diheteroarylamino group which may be substituted", "arylheteroarylamino group which may be substituted" in the formula (1), the groups described above as "aryl" and "heteroaryl" may be cited.

Specifically, there may be mentioned: diphenylamino, dinaphthylamino, phenylnaphthylamino, bipyrylamino, phenylpyridylamino, naphthylpyridylamino and the like.

The "alkyl" in the "alkyl" and the "alkyl which may be substituted" in the formula (1) may be either a straight chain or a branched chain, and examples thereof include a straight-chain alkyl group having 1 to 24 carbon atoms and a branched-chain alkyl group having 3 to 24 carbon atoms. Preferably an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), still more preferably an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), and particularly preferably an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms).

Specific examples of the "alkyl group" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 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.

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

As specific cycloalkyl groups, there may be mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms thereof, or norbornenyl, 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, diamantanyl, decahydronaphthyl, decahydroazulenyl, and the like.

Examples of the "alkenyl group" of the "alkenyl group which may be substituted" in the formula (1) include a linear alkenyl group having 2 to 24 carbon atoms and a branched alkenyl group having 4 to 24 carbon atoms. Preferably C2-18 alkenyl, more preferably C2-12 alkenyl, further preferably C2-6 alkenyl, especially preferably C2-4 alkenyl.

Specific examples of the "alkenyl group" include vinyl, allyl, and butadienyl groups.

Examples of the "alkoxy group" of the "alkoxy group which may be substituted" in the formula (1) include a linear alkoxy group having 1 to 24 carbon atoms and a branched alkoxy group having 3 to 24 carbon atoms. Preferably an alkoxy group having 1 to 18 carbon atoms (branched alkoxy group having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (branched alkoxy group having 3 to 12 carbon atoms), still more preferably an alkoxy group having 1 to 6 carbon atoms (branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (branched alkoxy group having 3 to 4 carbon atoms).

Specific "alkoxy" may include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

As the "aryloxy group" of the "aryloxy group which may be substituted" in the formula (1), a group in which hydrogen of an-OH group is substituted by an aryl group, which may refer to the group described as the "aryl group".

As the "arylthio group" of the "arylthio group which may be substituted" in the formula (1), a group in which hydrogen of-SH group is substituted with an aryl group which may be cited as the Ar ⁴And an "aryl" group in X.

Examples of the "silyl group which may be substituted" in the formula (1) include trialkylsilyl groups. As the "trialkylsilyl group", there may be mentioned groups in which three hydrogens of the silyl group are each independently substituted with an alkyl group, and the alkyl group may be cited as the Ar group⁴And the "alkyl" group in X. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclobutyl and the like.

Specific examples of the "trialkylsilyl group" include: trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, tri-sec-butylsilyl group, tri-tert-butylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl group, tert-butyldimethylsilyl group, methyldiethylsilyl group, propyldiethylsilyl group, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, tert-butyldiisopropylsilyl, and the like.

With respect to Ar in the formula (1)^c、Ar¹¹、Ar¹²、Ar¹³、Ar¹⁴、Ar¹⁵、Ar¹⁶、Ar¹⁷And Ar¹⁸Examples of the substituent in the case of "optionally substituted" include an alkyl group, an aryl group and a heteroaryl group. As the alkyl group, aryl group or heteroaryl group, the groups described above as "alkyl group", "aryl group" or "heteroaryl group" may be cited. The number of the substituent may be any number up to the maximum substitutable number, for example, preferably 0 to 3, more preferably 0 to 2, and further preferably 0 to 1. When a plurality of substituents are present, the plurality of substituents may be bonded to each other. For example, when the hydrogens of the methylene groups in the fluorenyl and benzofluorenyl groups are both substituted by phenyl groups, the phenyl groups may be bonded to each other by single bonds.

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

[ solution 36]

In the formulae (1-X1) to (1-X7), a represents a bonding position.

In the formulae (1-X1) to (1-X3), Ar²¹、Ar²²And Ar²³Each independently is hydrogen, phenyl, biphenyl, terphenylTetra-biphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl,

A triphenylene group, a pyrenyl group, an anthracenyl group, or a group represented by the formula (A) described later.

In the formulae (1-X4) to (1-X7), Ar²⁴、Ar²⁵、Ar²⁶、Ar²⁷And Ar²⁸Each independently is hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl,

In the formulae (1-X1) to (1-X7), in Ar²¹、Ar²²、Ar²³、Ar²⁴、Ar²⁵、Ar²⁶、Ar²⁷And Ar²⁸In the case of an anthracenyl group, at least one hydrogen in the anthracenyl group may be substituted by a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a,

A triphenylene group, a pyrenyl group, or a group represented by the formula (A) described later.

In addition, any one or more hydrogen of the groups represented by the formulas (1-X1) to (1-X7) may be substituted by an alkyl group having 1 to 6 carbon atoms (preferably methyl or tert-butyl).

Further, preferable examples of the "aryl group which may be substituted" include those selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, and the like,

Terphenyl group (particularly m-terphenyl-5' -yl group) substituted with at least one substituent group selected from the group consisting of a group, a triphenylene group, a pyrenyl group, and a group represented by the formula (A) described later.

The "heteroaryl group which may be substituted" may include a group represented by any one of the following formulae (a), (B), (C), (D) and (E).

In addition, as the "aryl group which may be substituted" or the "heteroaryl group which may be substituted", a group in which an aryl group or a heteroaryl group is bonded to a carbon atom adjacent to a carbon atom at a bonding position of the group is cited as a preferable example. Specifically, the base represented by the following formula (1-XB), and the base represented by the formula (1-X6) is an example of the base represented by the formula (1-XB).

[ solution 37]

In the formula (1-XB), Ar^B1Is an aryl group which may have a substituent or a heteroaryl group which may have a substituent, Ar^B1The bonded benzene ring may be condensed with other aryl or heteroaryl rings to form a fused ring, Ar^B2Is an aryl group which may have a substituent or a heteroaryl group which may have a substituent, Ar^B2An atomic bond with any one of the benzene ring or the fused ring, n is an integer of 0 to 2, and when n is 2, a plurality of Ar are present^B2May be the same or different. The dotted line represents the skeleton of an aryl ring or the skeleton of a heteroaryl ring which forms a condensed ring together with the benzene ring, and represents the bonding position of the group represented by formula (1-XB). In the formula (1-XB), "the substituent which may have a substituent" is an aryl group or a heteroaryl group. Formula (1-XB) preferably has at least one fused ring. For example, Ar is preferred^B1Condensation of the bonded benzene ring with other aryl or heteroaryl rings to form fused rings, or Ar^B1Or more than one Ar^B2Contain fused rings. Examples of the condensed 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, Ar¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸Are all hydrogen and are selected from the group consisting of Ar ^c、Ar¹⁴And Ar¹⁵At least one of the group consisting of the radicals represented by the formula (1-XB)The anthracene compound (c) is one of preferred embodiments. At this time, R^cHydrogen is preferred.

Specific examples thereof 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), (1-4254), (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), (1-3839), (1-4381), (1-4390), (1-3837), (1-3854), (1-4091), (1-3859), (1-4701), (1-4688), (1-4715), (1-4565), (1-4736), and (1-4112).

The anthracene-based compound represented by the formula (1) preferably has a substituent containing an anthracene ring as "aryl group which may be substituted" or "heteroaryl group which may be substituted".

For example, when Ar ¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, and Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸When both are hydrogen, it is also preferably selected from the group consisting of Ar^c、Ar¹⁴And Ar¹⁵At least one of the group consisting is an anthracycline-containing radical. At this time, R^cHydrogen is preferred.

As anthracycline-containing groups, there may be mentioned: an anthracene group which may have a substituent; is any one of formula (1-X1) to formula (1-X7), and Ar in the formula²¹、Ar²²、Ar²³、Ar²⁴、Ar²⁵、Ar²⁶Or Ar²⁷And/or Ar²⁸A group which is an anthracene group which may have a substituent; and a group represented by the formula (A) described later and selected from the group consisting of R²¹～R²⁸And R³⁹Any one or two of the groups are an anthracene group which may have a substituent, or the like.

Examples of the anthracene compound represented by the formula (1) include compounds represented by any of the following formulae.

[ solution 38]

In each of the formulae, X is independently an aryl group which may be substituted with an aryl group or a heteroaryl group, and A is independently an arylene group which may be substituted with a single bond, an aryl group or a heteroaryl group which may be substituted with an aryl group or a heteroaryl group. As regards aryl and heteroaryl, reference is made here to Ar of formula (1), respectively^cAnd the aryl and heteroaryl in the above.

Preferred examples of the aryl group of the above formula X include phenyl, 1-naphthyl and 2-naphthyl, and preferred examples of the heteroaryl group include a group represented by the formula (A). X is preferably unsubstituted aryl or unsubstituted heteroaryl, and when substituted is preferably substituted by one or two phenyl groups.

As the arylene and heteroarylene groups of the formula A, there may be mentioned those obtained by removing Ar as represented by the formula (1)^cAnd the aryl group and the heteroaryl group are each a divalent group obtained by hydrogenating any one of the groups described above. Preferred examples of the group include a 1, 3-phenylene group, a 1, 4-phenylene group, a 1, 6-naphthylene group, a 2, 5-naphthylene group, a 2, 6-naphthylene group, a 2, 7-naphthylene group, and a divalent group obtained by removing any hydrogen from the group represented by the formula (A). A is preferably unsubstituted arylene or unsubstituted heteroarylene, and when substituted is preferably substituted with one or two phenyl groups.

Specific examples thereof 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), and (1-3875).

In addition, specific examples of the "aryl group which may be substituted" and the "heteroaryl group which may be substituted" include substituents represented by the following structural formulae as symbols in table 1.

At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium. Examples of the "halogen" in the above case include fluorine, chlorine, bromine and iodine. Particularly preferred is a compound represented by formula (1) wherein all hydrogens are replaced with deuterium.

At Ar¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, and Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸Among the compounds represented by formula (1) which are both hydrogen, compounds in which at least one hydrogen is substituted with deuterium are preferred. In this case, the substitution position of deuterium is not limited. For example, at least R can be enumerated^cA compound being deuterium selected from the group consisting of Ar^cAnd Ar¹¹～Ar¹⁸A compound in which at least one hydrogen in at least one of the groups is substituted by deuterium, or a compound in which all hydrogens are substituted by deuterium, or the like.

In the formula (1), R^cIs hydrogen, alkyl or cycloalkyl, preferably hydrogen, methyl or tert-butyl, more preferably hydrogen.

On the other hand, when Ar is¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸When both are hydrogen, R may also be mentioned ^cPreferred examples of the anthracene compound are alkyl and cycloalkyl. Specific examples thereof include compounds represented by the following formula numbers in table 1: (1-4434), (1-4429), (1-4458), (1-4409), (1-4404) and (1-4427).

In the formula (1), Ar is preferred¹¹～Ar¹⁸At least two of which are aryl which may be substituted or heteroaryl which may be substituted. Namely, anthracene represented by the formula (1)The compound preferably has a structure in which at least three substituents selected from the group consisting of an optionally substituted aryl group and an optionally substituted heteroaryl group are bonded to an anthracene ring.

The anthracene compound represented by the formula (1) is more preferably Ar¹¹～Ar¹⁸Two of which are aryl which may be substituted or heteroaryl which may be substituted, and the other six of which are hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted or alkoxy which may be substituted. That is, the anthracene compound represented by the formula (1) more preferably has a structure in which three substituents selected from the group consisting of an aryl group which may be substituted and a heteroaryl group which may be substituted are bonded to an anthracene ring.

The anthracene compound represented by the formula (1) is preferably Ar¹¹～Ar¹⁸Any two of which are optionally substituted aryl or optionally substituted heteroaryl, and the other six of which are hydrogen, methyl or tert-butyl. Particularly preferably Ar ¹¹～Ar¹⁸Any two of which are optionally substituted aryl or optionally substituted heteroaryl, R^cIs hydrogen, and Ar¹¹～Ar¹⁸The other six of which are hydrogen.

The anthracene compound represented by the formula (1) may be defined as a preferred range, and the anthracene compound represented by the following formula (1A), formula (1B), formula (1C), formula (1D), or formula (1E) may be defined as well.

[ solution 39]

In the formula (1A), the formula (1B), the formula (1C), the formula (1D) and the formula (1E), Ar^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' and Ar¹⁸' independently of one another are phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, quaterphenyl, naphthyl,

A group, a triphenylene group, a pyrenyl group or those represented by the formula (A) described laterAt least one hydrogen in the group may be selected from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, fluorenyl, and the like,

A triphenylene group, a pyrenyl group, or a group represented by the formula (A) described later. Here, when the hydrogens of the methylene groups in the fluorenyl and benzofluorenyl groups are both substituted by phenyl groups, the phenyl groups may be bonded to each other by a single bond. In the absence of a bond Ar^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' and Ar¹⁸Instead of hydrogen, the carbon atom of the anthracycline of' may be bonded with a methyl group or a tert-butyl group.

When Ar is^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' and Ar¹⁸' when each is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, a group represented by any one of the above-mentioned formulae (1-X1) to (1-X7) is preferable.

Ar^c'、Ar¹¹'、Ar¹²'、Ar¹³'、Ar¹⁴'、Ar¹⁵'、Ar¹⁷' and Ar¹⁸'are each independently more preferably a phenyl group, a biphenyl group (particularly, biphenyl-2-yl group or biphenyl-4-yl group), a terphenyl group (particularly, m-terphenyl-5' -yl group), a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any of the formulae (a-1) to (a-4) described later, in which case at least one hydrogen of these groups may be substituted by a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any of the formulae (a-1) to (a-4) described later.

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

The group represented by the formula (A) will be described below.

[ solution 40]

In the formula (A), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (A), R²¹～R²⁸Each independently hydrogen, alkyl which may be substituted, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ²¹～R²⁸Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In addition, at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group.

The group represented by formula (a) is a group obtained by removing one hydrogen at any position of formula (a), and represents the position.

R in the formula (A)²¹～R²⁸Preferably, all are hydrogen, or at least one is an aryl or heteroaryl group which may be substituted, more preferably all are hydrogen, or at least one is an aryl or heteroaryl group which may be substituted and the others are hydrogen, and even more preferably all are hydrogen, or any one or two are an aryl or heteroaryl group which may be substituted and the others are hydrogen. When R is²¹～R²⁸In the case where adjacent groups are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, it is preferable that the hydrogen in the formed ring is not substituted by a substituent and the remaining R ²¹～R²⁸Is hydrogen, or a substituent replacing hydrogen in the ring formed and the remainder of R²¹～R²⁸At least one of which is an aryl group which may be substituted or a hetero group which may be substitutedAryl, more preferably the hydrogen in the ring formed is unsubstituted by a substituent and the remainder of R²¹～R²⁸Is hydrogen, or a substituent replacing hydrogen in the ring formed and the remainder of R²¹～R²⁸One or both of which are aryl which may be substituted or heteroaryl which may be substituted.

As R in formula (A)²¹～R²⁸The "alkyl group" of the "alkyl group which may be substituted" in (1) may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms and a branched alkyl group having 3 to 24 carbon atoms. Preferably an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), still more preferably an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), and particularly preferably an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms).

As R in formula (A)²¹～R²⁸The "aryl group" of the "aryl group which may be substituted" in (1) includes, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms.

Specific "aryl" groups include: phenyl as a monocyclic system; biphenyl as a bicyclic ring system; naphthyl as the condensed bicyclic system; terphenyl (m-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic system; anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl as condensed tricyclic systems; triphenylene, pyrenyl, tetracenyl, benzofluorenyl as condensed quaternary ring systems; perylene groups and pentacene groups as condensed five-ring systems, and the like.

As R in formula (A)²¹～R²⁸Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" in (1) include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, still more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Specific examples of the "heteroaryl group" include: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzo [ b ] thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuryl, naphthobenzothienyl, and the like.

As R in formula (A)²¹～R²⁸Examples of the "alkoxy group" of the "alkoxy group which may be substituted" in (1) include a linear alkoxy group having 1 to 24 carbon atoms and a branched alkoxy group having 3 to 24 carbon atoms. Preferably an alkoxy group having 1 to 18 carbon atoms (branched alkoxy group having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (branched alkoxy group having 3 to 12 carbon atoms), still more preferably an alkoxy group having 1 to 6 carbon atoms (branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (branched alkoxy group having 3 to 4 carbon atoms).

As R in formula (A)²¹～R²⁸The "aryloxy group" of the "aryloxy group which may be substituted" in (1) is a group in which hydrogen of the-OH group is substituted by an aryl group which may be cited as R²¹～R²⁸The "aryl" in (1).

As R in formula (A)²¹～R²⁸The "arylthio group" of the "arylthio group which may be substituted" in (1) is a group in which hydrogen of the-SH group is substituted with an aryl group, which may be cited as R²¹～R²⁸The "aryl" in (1).

As R in formula (A)²¹～R²⁸As the "trialkylsilyl group" in (1), there can be mentioned groups in which three hydrogens in the silyl group are each independently substituted by an alkyl group, and the alkyl group may be referred to as R²¹～R²⁸The "alkyl" in (1) or (b). Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclobutyl and the like.

As R in formula (A)²¹～R²⁸The "substituted amino group" of the "amino group which may be substituted" in (1) includes, for example, an amino group in which two hydrogens are substituted with an aryl group or a heteroaryl group. The amino group with two hydrogens substituted by aryl is the amino group substituted by diaryl, the amino group with two hydrogens substituted by heteroaryl is the amino group substituted by diheteroaryl, and the amino group with two hydrogens substituted by aryl and heteroaryl is the amino group substituted by arylheteroaryl. The aryl or heteroaryl groups may be referred to as R²¹～R²⁸The "aryl" or "heteroaryl" in (1).

Specific "substituted amino group" includes: diphenylamino, dinaphthylamino, phenylnaphthylamino, bipyrylamino, phenylpyridylamino, naphthylpyridylamino and the like.

As R in formula (A)²¹～R²⁸Examples of the "halogen" in (1) include: fluorine, chlorine, bromine, iodine.

As R in formula (A)²¹～R²⁸In the groups described above, some of the groups may be substituted as described above, and examples of the substituent in the above-described case include an alkyl group, an aryl group, and a heteroaryl group. The alkyl, aryl or heteroaryl groups may be referred to as R²¹～R²⁸The "alkyl", "aryl" or "heteroaryl" in (1).

"> N-R as Y in formula (A) ³⁹R in `³⁹Is hydrogen or a substituted aryl group, and as said aryl group, the reference may be made to R²¹～R²⁸The substituent mentioned for the "aryl" in (1) may be cited as the substituent mentioned for R²¹～R²⁸The substituent(s) of (1).

R in the formula (A)²¹～R²⁸Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where no ring is formed is a group represented by the following formula (A-1), and the case where a ring is formed is, for example, a group represented by the following formulae (A-2) to (A-14). Furthermore, any one of the groups represented by the formulae (A-1) to (A-14) isAt least one hydrogen may be substituted by alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy or cyano, as may be cited for R²¹～R²⁸The groups in (1) above.

Examples of the ring in which adjacent groups are bonded to each other include a hydrocarbon ring, a cyclohexane ring, and an aryl ring or a heteroaryl ring²¹～R²⁸The "aryl" or "heteroaryl" in (1) is a ring structure formed by condensation with one or two benzene rings in the formula (A-1).

Examples of the group represented by formula (A) include a group represented by any one of formulae (A-1) to (A-14), preferably a group represented by any one of formulae (A-1) to (A-11), more preferably a group represented by any one of formulae (A-1) to (A-4), still more preferably a group represented by any one of formulae (A-1), (A-3) and (A-4), and most preferably a group represented by formula (A-1).

[ solution 41]

The group represented by formula (a) is a group obtained by removing one hydrogen at any position of formula (a), and represents the position. That is, the group represented by the formula (A) may have an arbitrary position as a bonding position. Among them, preferred are arbitrary carbon atoms on two benzene rings in the structure of formula (A), and R in the structure of formula (A)²¹～R²⁸Wherein adjacent groups are bonded to each other to form an arbitrary ring atom, or with "> N-R as Y in the structure of the formula (A)³⁹The N in "is a group directly bonded (having a bond in these).

Y in the formula (A) and Y in each of the formulae (A-1) to (A-14) are preferably-O-.

Examples of the group represented by the formula (a) include groups represented by the following formulae. Y and x in the formula are the same as defined above, and Y is preferably-O-.

[ solution 42]

The compound containing the group represented by the formula (a) (particularly, the group represented by the formula (a) wherein Y is — O-) can be cited as a preferable example of the anthracene compound represented by the formula (1), and the anthracene compound of the following (a) or (b) is preferable in addition to the compounds already described.

(a) In the formula (1), Ar¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸Are each hydrogen, selected from Ar^c、Ar¹⁴And Ar¹⁵At least one of the group consisting of a group represented by the formula (A) and selected from R in the formula (A)²¹～R²⁸And Y is > N-R³⁹R in the case of (1)³⁹At least one of the group consisting of an aryl or heteroaryl anthracene compound. R^cHydrogen is preferred.

Specific examples thereof 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 the formula (1), Ar¹⁴、Ar¹⁵Is optionally substituted aryl or optionally substituted heteroaryl, Ar¹¹、Ar¹²、Ar¹³、Ar¹⁶、Ar¹⁷And Ar¹⁸Are all hydrogen and are selected from the group consisting of Ar^c、Ar¹⁴And Ar¹⁵At least one of the groups is an aryl group having a group represented by the formula (A) as a substituent or an anthracene compound having a heteroaryl group having a group represented by the formula (A) as a substituent. R^cHydrogen is preferred. As a group represented by the formula (A)Examples of the substituted aryl group include groups represented by any one of the formulae (1-X1) to (1-X6), wherein Ar is represented by the formula ²¹、Ar²²、Ar²³、Ar²⁴、Ar²⁵Or Ar²⁶Is a group represented by the formula (A).

Specific examples thereof 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), (1-4047), (1-3778), (1-4168) and (1-4510).

The following describes the group represented by the above formula (B), the group represented by the above formula (C), the group represented by the above formula (D), and the group represented by the above formula (E). The following description of the substituents refers to R of formula (A)²¹～R²⁸And (4) description.

[ solution 43]

In the formula (B), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (B), R²⁹～R³⁸Each independently hydrogen, alkyl which may be substituted, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R²⁹～R³⁸Wherein adjacent groups 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 may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group Alkyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano. The group represented by formula (B) is a group obtained by removing one hydrogen at any position of formula (B), and represents the position.

In the formula (B), Y is preferably-O-.

R in the formula (B)²⁹～R³⁸Preferably, all are hydrogen, or at least one is an aryl or heteroaryl group which may be substituted, more preferably all are hydrogen, or at least one is an aryl or heteroaryl group which may be substituted and the others are hydrogen, and even more preferably all are hydrogen, or any one or two are an aryl or heteroaryl group which may be substituted and the others are hydrogen. When R is²⁹～R³⁸In the case where adjacent groups are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, it is preferable that the hydrogen in the formed ring is not substituted by a substituent and the remaining R²⁹～R³⁸Is hydrogen, or a substituent replacing hydrogen in the ring formed and the remainder of R²⁹～R³⁸At least one of which is an aryl group which may be substituted or a heteroaryl group which may be substituted, more preferably the hydrogen in the ring formed is not substituted by a substituent and the remainder of R²⁹～R³⁸Is hydrogen, or a substituent replacing hydrogen in the ring formed and the remainder of R²⁹～R³⁸One or both of which are aryl which may be substituted or heteroaryl which may be substituted.

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

[ solution 44]

More specifically, the group represented by the following formula is exemplified as the group represented by the formula (B). Y and x in the formula are the same as defined above, and Y is preferably-O-.

[ solution 45]

In the formula (C), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (C), R⁴¹～R⁴⁸Each independently hydrogen, alkyl which may be substituted, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R⁴¹～R⁴⁸Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In addition, at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group.

The group represented by formula (C) is a group obtained by removing one hydrogen at any position of formula (C), and represents the position.

In the formula (C), when Y is > N-R³⁹When R is³⁹Preferably phenyl which may be substituted, more preferably unsubstituted. As R³⁹Optionally substituted phenyl of (A) may be substituted with R⁴²、R⁴³、R⁴⁶Or R⁴⁷As a bond to a benzene ring. Y is preferably at least one-O-, more preferably any one Y is-O-, or any one Y is-O-, and the other is > N-R³⁹. Preferably R⁴¹～R⁴⁸Are all hydrogen.

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

[ solution 46]

More specifically, the group represented by the following formula is exemplified as the group represented by the formula (C). Y and x in the formula are the same as defined above, and Y is preferably-O-.

[ solution 47]

In the formula (D), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (D), R⁵¹～R⁵⁸Each independently hydrogen, alkyl which may be substituted, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ⁵¹～R⁵⁸Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In addition, at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group.

The group represented by formula (D) is a group obtained by removing one hydrogen at any position of formula (D), and represents the position.

In the formula (D), Y is preferably-O-. Preferably R⁵¹～R⁵⁸Are all hydrogen.

In formula (E), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (E), R⁶¹～R⁷¹Each independently is hydrogen, may be substitutedSubstituted alkyl, cycloalkyl which may be 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ⁶¹～R⁷¹Wherein adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In addition, at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group.

The group represented by formula (E) is a group obtained by removing one hydrogen at any position of formula (E), and represents the position.

In the formula (E), when Y is > N-R³⁹When R is³⁹Preferably phenyl which may be substituted, more preferably unsubstituted. As R³⁹Optionally substituted phenyl of (A) may be substituted with R⁶¹、R⁶²、R⁶⁹Or R⁷⁰As a bond to a benzene ring. Preferably, at least one of Y is-O-, and more preferably both are-O-. R⁶¹～R⁷¹Preferably hydrogen, phenyl, biphenyl or naphthyl, more preferably both hydrogen.

An anthracene compound represented by the following formula (1Aa) is particularly preferable.

[ solution 48]

A phenyl group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulae (A-1) to (A-11), wherein at least one hydrogen in these groups may be represented by a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a naphthoyl group, a,

A triphenylene group, a pyrenyl group, or a group represented by any one of the formulae (A-1) to (A-11). Here, when the hydrogens of the methylene groups in the fluorenyl and benzofluorenyl groups are both substituted by phenyl groups, the phenyl groups may be bonded to each other by a single bond. In addition, Ar is not bonded^c'、Ar¹⁴' and Ar¹⁵In place of hydrogen, a methyl group or a tert-butyl group may be substituted on a carbon atom of the anthracycline of' in place of hydrogen. At least one hydrogen in the compound represented by formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (1Aa) may be substituted with deuterium.

In the formula (1Aa), Ar^c'、Ar¹⁴' and Ar¹⁵' is preferably, independently of each other, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group or a group represented by any one of the formulae (A-1) to (A-4), and at least one hydrogen of these groups may be substituted by a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group or a group represented by any one of the formulae (A-1) to (A-4).

In the compound represented by the formula (1Aa), it is preferable that at least the carbon at the 10-position of the anthracene ring (Ar to which Ar is bonded) is to be bonded^cThe carbon of' is considered to be the 9-position) bonded hydrogen is substituted with deuterium. That is, the compound represented by the formula (1Aa) is preferably a compound represented by the following formula (1 Ab). In the formula (1Ab), D is deuterium, Ar^c'、Ar¹⁴' and Ar¹⁵' is the same as defined in formula (1 Aa). D in formula (1Ab) represents that at least the position is deuterium, and any other hydrogen or more than one hydrogen in formula (1Aa) is deuterium at the same time, and it is further preferable that all the hydrogen in formula (1Aa) is deuterium.

[ solution 49]

Specific examples of the compounds represented by formula (1) include compounds represented by formulae (1-1) to (1-5179) shown in table 1 below. However, the invention is not limited by the disclosure of these specific structures. In table 1, D represents deuterium, Me represents methyl, tBu represents t-butyl, CyHex represents cyclohexyl, and other symbols will be described later.

[ Table 1]

The substituents represented by symbols used in table 1 are shown below. The notation that Y is O in the notation attached to the structural formula of the substituent shown below indicates a substituent that-Y-is-O-in the structural formula (for example, HCO-1) when the notation that Y is S is shown in Table 1, indicates a substituent that-Y-is-S-in the structural formula (for example, HCS-1) when the notation that Y is S is shown in Table 1, and indicates a substituent that-Y-is > N-Ph (Ph is phenyl) (for example, HCN-1) in the structural formula when the notation that Y is N is shown in Table 1. In addition, when the structural formula of the substituent shown below is additionally provided with a symbol in which Z is O, the symbol represents a substituent in which-Z-in the structural formula is-O- (e.g., DHCO-1), when Z is S, the symbol represents a substituent in which-Z-in the structural formula is-S- (e.g., DHCS-1), and when Z is N, the symbol represents that-Z-in the structural formula is > N-C ₆D₅A substituent of (e.g., DHCN-1). In the following structural formulae, D represents deuterium, Me represents a methyl group, tBu represents a tert-butyl group, and x represents a bonding position.

[ solution 50]

[ solution 51]

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[ Hua 53]

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[ chemical 59]

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[ solution 71]

[ chemical formula 72]

[ solution 73]

[ chemical formula 74]

[ solution 75]

[ 76]

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[ solution 91]

[ solution 92]

[ solution 93]

Among the compounds, preferred is a compound represented by the following formula. In the following formula, D represents deuterium, Me represents methyl, tBu represents t-butyl, and CyHex represents cyclohexyl.

[ solution 94]

[ solution 95]

[ solution 96]

[ solution 97]

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[ solution 113]

[ chemical formula 114]

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[ solution 117]

[ chemical formula 118]

[ solution 119]

[ chemical formula 120]

[ solution 121]

[ chemical formula 122]

[ solution 123]

1-1-2. Anthracene Compound production method

The anthracene compound represented by the formula (1) can be produced by a method according to the production method described in International publication No. 2006/003842, Korean laid-open patent publication No. 2017-116885, International publication No. 2009/142230, or the like.

1-2-1 polycyclic aromatic compound represented by formula (2) and multimer thereof

The organic EL element of the present invention includes, as a dopant material, a polycyclic aromatic compound represented by the following formula (2) and a polymer of a plurality of polycyclic aromatic compounds having a structure represented by the formula (2) in a light-emitting layer. The polycyclic aromatic compound is preferably a polycyclic aromatic compound represented by the following formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f).

[ solution 124]

In each structural formula, "a" to "C" and "a" to "C" are each a symbol representing a ring structure represented by a ring, a benzene ring, or a five-membered ring, and the other symbols are as defined above.

The a ring, the B ring and the C ring in formula (2) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted by a substituent. The substituent is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl group and a heteroaryl group), a substituted or unsubstituted diarylboron group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group, or a substituted silane group. Examples of the substituent in the case where these groups have a substituent include: aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl.

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

Ring a, ring B and ring C are preferably at least one of an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, more preferably, ring a, ring B and ring C are each an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and further preferably, ring a, ring B and ring C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

As the substituent at this time, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl group and a heteroaryl group), a substituted or unsubstituted diarylboron group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group is preferable. Examples of the substituent in the case where these groups have a substituent include: aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, substituted silyl.

In particular, the substituent is preferably a cycloalkyl group such as a substituted or unsubstituted alkyl group (in particular, a neopentyl group) or an adamantyl group. Further, a tertiary alkyl group (tR) is preferable. This is because such bulky substituents prevent inactivation due to aggregation of molecules, and increase the luminescence quantum yield (photoluminescence quantum yield, PLQY). Further, as the substituent, a substituted or unsubstituted diarylamino group is also preferable.

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

[ solution 125]

In the formula (tR), R^a、R^bAnd R^cEach independently represents an alkyl group having 1 to 24 carbon atoms, wherein-CH is optionally contained in the alkyl group₂-may be substituted by-O-where the group represented by formula (tR) is substituted with at least one hydrogen in the compound or structure represented by formula (2).

As R^a、R^bAnd R^cThe "C1-24 alkyl group" may be either a straight chain or a branched chain, and examples thereof include a C1-24 straight chain alkyl group, a C3-24 branched chain alkyl group, a C1-18 alkyl group (C3-18 branched chain alkyl group), a C1-12 alkyl group (C3-12 branched chain alkyl group), a C1-6 alkyl group (C3-6 branched chain alkyl group), and a C1-4 alkyl group (C3-4 branched chain alkyl group).

R in formula (tR) of formula (2)^a、R^bAnd R^cThe total number of carbon atoms of (A) is preferably 3 to 20 carbon atoms, and particularly preferably carbonThe number is 3 to 10.

As R^a、R^bAnd R^cSpecific examples of the alkyl group of (1) include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 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.

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

Other preferable examples of the substituent in the ring a, ring B and ring C include a diarylamino group substituted with a group of the formula (tR), a carbazolyl group substituted with a group of the formula (tR) or a benzocarbazolyl group substituted with a group of the formula (tR). The "diarylamino group" includes groups described as the "first substituent" described below. Examples of the substitution pattern of the group of formula (tR) for the diarylamino group, the carbazolyl group, and the benzocarbazolyl group include those in which some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

Aryl ring in ring A, ring B and ring COr heteroaryl ring preferably having a structure corresponding to a ring containing "B", "X" or "B", "X", or a salt thereof¹"and" X²"the condensed bicyclic structure in the center of formula (2)" has a bonded five-membered ring or six-membered ring in common.

Here, the term "condensed bicyclic structure" means a structure containing "B" and "X" represented at the center of formula (2)¹"and" X²"two saturated hydrocarbon rings condensed. The "six-membered ring bonded in common to the condensed bicyclic structure" means, for example, a ring a (benzene ring (six-membered ring)) condensed with the condensed bicyclic structure as shown 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 phrase "the aryl ring or the heteroaryl ring has the above-mentioned six-membered ring" (as a ring a) "means that the ring a is formed only from the above-mentioned six-membered ring, or that another ring is further condensed in the above-mentioned six-membered ring so as to include the above-mentioned six-membered ring, or the like. In other words, the "aryl ring or heteroaryl ring having a six-membered ring (as A ring)" as used herein means that a six-membered ring constituting all or a part of the A ring is condensed with the condensed bicyclic structure. The same applies to the "five-membered ring". The same description applies to "ring B (ring B)" and "ring C (ring C)".

The ring A in the formula (2) corresponds to the ring a 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) and a substituent R thereof¹Substituent R³. The ring B in the formula (2) corresponds to the ring B in the formulae (2-a), (2-B) and (2-c) and the substituent R thereof⁸Substituent R¹¹The b ring in the formula (2-d) and a substituent R thereof¹⁰And a substituent R¹¹And the b-ring in the formula (2-e) and the formula (2-f) and the substituent R thereof⁸And a substituent R⁹. The C ring in formula (2) corresponds to the C ring in formula (2-a) and its substituent R⁴Substituent R⁷The c-ring in the formula (2-b), the formula (2-d) and the formula (2-f) and a substituent R thereof⁴And a substituent R⁵And the c-ring in formula (2-c) and formula (2-e) and its substituent R⁶And a substituent R⁷. That is, the formula (2-a) corresponds to a structure in which a ring having at least a six-membered ring structure is selected as the A ring to C ring of the formula (2), and the formula (2-b), the formula (2-C), the formula (2-d), the formula (2-e) and the formula(2-f) correspond to the structures in which the ring having at least a six-membered ring structure and the ring having at least a five-membered ring structure are selected as the A ring to the C ring of formula (2), respectively. Each ring in the formula (2-a) and the like is represented by a lowercase letter a to c in the above-mentioned meaning.

X in the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f)_XEach independently > O, > S, > N-R or > C (-R) ₂. Here, R of the > N-R is an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted cycloalkyl group, preferably an optionally substituted aryl group, more preferably an unsubstituted aryl group. Additionally, the > C (-R)₂Each R of (a) is independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, preferably alkyl, more preferably methyl. > C (-R)₂Preferably, both R in (a) are the same. Additionally, > C (-R)₂Two R in (2) are also preferably mutually forming a ring.

X_XIndependently of each other, is preferably > O, > S or > N-R, more preferably > O or > S, and still more preferably > S.

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), R¹～R¹¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

R¹～R¹¹Each independently is preferably hydrogen, an alkyl group (particularly the tertiary alkyl group (tR), neopentyl group, etc.), a cycloalkyl group (e.g., adamantyl group, etc.), a substituted or unsubstituted diarylamino group, or a substituted silyl group (triphenylsilyl group, trimethylsilyl group, etc.).

Preferably: r of 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)¹～R³In the above-mentioned formula, 0 to 1 is a group other than hydrogen (particularly, the above-mentioned preference isAnd others are hydrogen, R⁴～R⁷In which 0 to 1 are a group other than hydrogen (particularly the above-mentioned preferred substituents) and the others are hydrogen, R⁸～R¹¹Of these, 0 to 1 are a group other than hydrogen (particularly, the above-mentioned preferred substituent) and the others are hydrogen,

more preferably: r¹～R³Wherein 1 is a group other than hydrogen (particularly the preferred substituents) and the others are hydrogen, R⁴～R⁷Wherein 1 is a group other than hydrogen (particularly the preferred substituents) and the others are hydrogen, R⁸～R¹¹In (1) is a group other than hydrogen (particularly, the preferred substituent) and the others are 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 substituent R of the ring a, the ring b and the ring c¹A substituent R²A substituent R³A substituent R⁴A substituent R⁵A substituent R⁶A substituent R⁷A substituent R⁸A substituent R⁹A substituent R¹⁰And a substituent R¹¹May be bonded to each other and together with the a-, b-or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl group, at least one of which may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group.

For example, the compound represented by the formula (2-a) has a structure of a ring constituting the compound changed depending on the bonding form among substituents in the a ring, the b ring and the c ring, as shown in the following formulae (2-a-1) and (2-a-2). The A ' ring, B ' ring and C ' ring in the formulae correspond to the A ring, B ring and C ring in formula (2), respectively. In addition, R in each formula¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹、a、b、c、X¹And X²Is the same as defined in the formula (2-a).

[ solution 126]

When the formula (2-a) is used for illustration, the A ' ring, the B ' ring and the C ' ring in the formula (2-a-1) and the formula (2-a-2) represent a substituent R¹A substituent R²A substituent R³A substituent R⁴A substituent R⁵A substituent R⁶A substituent R⁷A substituent R⁸A substituent R⁹A substituent R¹⁰And a substituent R¹¹The adjacent groups in (b) are bonded to each other and form an aryl ring or a heteroaryl ring together with the a-ring, the b-ring and the c-ring, respectively (may also be referred to as a condensed ring in which another ring structure is condensed with the a-ring, the b-ring or the c-ring). Although not shown in the formula, there are also compounds in which all of the a, B and C rings are changed to a ' ring, B ' ring and C ' ring. As is apparent from the formulae (2-a-1) and (2-a-2), for example, R in the b ring⁸R with ring c⁷R of ring b¹¹R with ring a¹R of ring c⁴R with ring a³Etc. do not correspond to "adjacent groups to each other", these are not bonded. That is, "adjacent groups" means groups adjacent to each other on the same ring.

The compound represented by the formula (2-a-1) or the formula (2-a-2) corresponds to, for example, compounds represented by the formulae (2-67) to (2-74), the formulae (2-76) to (2-83), the formulae (2-273) to (2-276), the formulae (2-290) to (2-295), and the formulae (2-350) to (2-355), which are specific compounds described later, and the like. That is, for example, a compound having an a 'ring (or B' ring or C 'ring) formed by condensation of a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring or an indene ring with respect to a benzene ring as the a ring (or B ring or C ring) in formula (2-a), and the fused ring a' (or fused ring B 'or fused ring C') formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring or a fluorene ring, respectively.

In the formulae (2-b), (2-c), (2-d), (2-e) and (2-f), a condensed ring in which another ring structure is condensed with the a-ring, the b-ring or the c-ring may be formed in the same manner. For example, the benzene ring as the a-ring or b-ring may be condensed with another ring structure to form a condensed ring, similarly to the benzene ring in the formula (1-a).

In the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f), R is particularly preferably in a five-membered ring as a b-ring or a c-ring ⁴～R¹¹Adjacent groups in (1) are bonded to each other to form a ring to form a condensed ring. For example, in the c-rings of the formulae (2-b) and (2-c), the b-rings and the c-rings of the formulae (2-d), (2-e) and (2-f), by R³～R¹¹The adjacent groups in (1) are bonded to each other to form a ring, and a B 'ring or a C' ring as a condensed ring may be formed. Examples of the condensed ring in the case where the ring to be 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 following formulae (2 to 572) to (1 to 588).

For example, in formula (2-b), formula (2-c), formula (2-d), formula (2-e) and formula (2-f), for example, when X is_XWhen the number 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 condensation of a benzene ring with respect to the furan ring is a benzofuran ring.

Further, for example, in the formulae (2-b), (2-c), (2-d), (2-e) and (2-f), when X is_XWhen the value is > S, the B-ring or C-ring is a thiophene ring, and a ring corresponding to the B 'ring or C' ring of the formula (2-a-1) formed by condensation of a benzene ring with respect to the thiophene ring is a benzothiophene ring.

As an example, R in a five-membered ring which is a c-ring of the formula (2-b)⁴And R⁵And bonded to each other to form a benzene ring to form a condensed ring.

[ solution 127]

In the formula (2-b-1), R¹、R²、R³、R⁸、R⁹、R¹⁰、R¹¹、X_X、Y¹、X¹And X²The same meanings as in the formula (2-b), respectively, and the preferred ranges are also the same. R^4b、R^5b、R^6b、R^7bIs a substituent selected from the group consisting of hydrogen or an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl group, at least one of which may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group. Preferably: r^4b、R^5b、R^6b、R^7bIn the above formula, 0 to 2 of the substituents are other than hydrogen and the others are hydrogen, and more preferably 1 of the substituents is other than hydrogen and the others are hydrogen. As the substituent other than hydrogen, the preferable range can be referred to the description of the substituent described later as the first substituent (which may have the second substituent). The substituent other than hydrogen is particularly preferably an alkyl group (particularly, the above-mentioned tertiary alkyl group (tR), neopentyl group, etc.), a cycloalkyl group (e.g., adamantyl group, etc.), or a substituted or unsubstituted diarylamino group.

X in the formula (2)¹And X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, said > C (-R) ₂R of (a) is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, R of said > N-R and/or said > C (-R)₂R of (2) may be bonded to the B ring and/or the C ring by a linking group or a single bond, and the linking group is preferably-O-, -S-or-C (-R)₂-. Furthermore, the "-C (-R)₂R of the-is hydrogen, alkyl or cycloalkyl. The same applies to X in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f)¹And X²。

In the formula (2), 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), X¹And X²Independently of one another, is preferably > O or > N-R, more preferably > N-R with R being optionally substituted phenyl, even more preferably > N-R with at least one R being one or two tert-butyl, tert-pentyl, methyl or phenyl substituted phenyl, and especially preferably > N-R with at least one R being one tert-butyl or tert-pentyl substituted phenyl. X¹And X²The groups may be the same as each other or different.

Here, "> R of N-R and/or-C (-R) in the formula (2)₂The definition that R of (A) is bonded to the A ring, the B ring and/or the C ring by a linking group or a single bond "corresponds to R and/or-C (-R) of" > N-R in the formulae (2-a), (2-B), (2-C), (2-d), (2-e) and (2-f) ₂R of-is selected from-O-, -S-, -C (-R)₂-or a single bond to the a-ring, the b-ring and/or the c-ring.

The definition can be expressed by a compound represented by the following formula (2-a-3-1) and having X¹Or X²A ring structure introduced into the condensed rings B 'and C'. I.e. for example with other rings to introduce X¹(or X)²) The compound of (1) is a compound of ring B ' (or ring C ') (ring B ') formed by condensation of benzene rings of ring B (or ring C) in the formula (2-a). The condensed ring B '(or the condensed ring C') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

The above-mentioned definition may be expressed by a compound represented by the following formula (2-a-3-2) or formula (2-a-3-3) and having X¹And/or X²A ring structure introduced into the condensed ring A'. I.e. for example with other rings to introduce X¹(and/or X)²) The compound of formula (2-a) has an A' ring formed by condensation of a benzene ring as the a ring. The condensed ring A' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

[ solution 128]

As ring A of formula (2)Examples of the "aryl ring" of the ring B and the ring C include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. Further, the "aryl ring" corresponds to the benzene ring 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), and "R ¹～R¹¹An aryl ring "in which adjacent groups in (a) are bonded to each other and form together with the a-ring, the b-ring, or the c-ring.

Specific "aryl ring" may include: a benzene ring as a monocyclic system; a biphenyl ring as a bicyclic system; naphthalene rings and tetrahydronaphthalene rings as condensed bicyclic systems; a tribiphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic system; anthracyclines, acenaphthenes, fluorenes, phenalenes, phenanthrenes as condensed tricyclic systems; a triphenylene ring, a pyrene ring, and a quaterrylene ring as a condensed quaternary ring system; perylene rings, pentacene rings and the like as the condensed five-ring systems.

Examples of the "heteroaryl ring" of the a ring, B ring and C ring of formula (2) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon. Further, the "heteroaryl ring" corresponds to a five-membered ring 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), and "R ¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹And a heteroaryl ring "wherein adjacent groups in (a) are bonded to each other and form together with the a, b, or c ring.

Specific examples of the "heteroaryl ring" include: a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline (cinnoline) ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxazine ring, a phenothiazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, an anthracene ring, and the like.

In the above, "aryl ring" and "heteroaryl ring" as the a, B and C rings may be bonded in common at any position to the condensed bicyclic structure at the center of formula (2). 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 formula (1). As described above, the ring A, ring B and ring C preferably have and contain B, X ¹And X²The condensed bicyclic structure in the center of formula (2) has a bonded five-membered ring or six-membered ring in common. That is, for example, in the formula (2-a), R is preferably represented by¹～R³、R⁴～R⁷And R⁸～R¹¹Wherein adjacent groups in (a) are bonded to each other and form an aryl ring or a heteroaryl ring together with the a-ring, the b-ring or the c-ring (the benzene ring as a six-membered ring is bonded in common to the condensed bicyclic structure at the center of formula (2)), and R of formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f)⁴～R¹¹In (2) are bonded to each other and form an aryl ring or a heteroaryl ring together with the b-ring and the c-ring (the five-membered ring is bonded in common to the condensed bicyclic structure in the center of formula (2)). Examples of the five-membered ring in this case include a pyrrole ring, a furan ring, and a thiophene ring.

At least one of the "aryl ring" or "heteroaryl ring" may be substituted with a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl" (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted silyl group as a first substituent, an aryl group of "aryl" or "heteroaryl", "diarylamino", a heteroaryl group of "diheteroarylamino", a substituted or unsubstituted "aryl group", a, The aryl and heteroaryl groups of the "arylheteroarylamino group", the aryl group of the "diarylboryl group", and the aryl group of the "aryloxy group" may be exemplified by the monovalent radicals of the "aryl ring" or the "heteroaryl ring".

The "alkyl group" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a straight-chain alkyl group having 1 to 24 carbon atoms and a branched-chain alkyl group having 3 to 24 carbon atoms. Preferably an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), still more preferably an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), and particularly preferably an alkyl group having 1 to 5 carbon atoms (branched alkyl group having 3 to 5 carbon atoms).

Specific examples of the alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 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.

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

As specific cycloalkyl groups, there may be mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms thereof, or norbornyl, 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, decahydronaphthyl, decahydroazulenyl, and the like.

Examples of the "alkoxy" as the first substituent include a linear alkoxy group having 1 to 24 carbon atoms and a branched alkoxy group having 3 to 24 carbon atoms. Preferably an alkoxy group having 1 to 18 carbon atoms (branched alkoxy group having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (branched alkoxy group having 3 to 12 carbon atoms), still more preferably an alkoxy group having 1 to 6 carbon atoms (branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (branched alkoxy group having 3 to 4 carbon atoms).

Specific examples of the alkoxy group include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

Examples of the "substituted silyl group" as the first substituent include a silyl group substituted with three substituents selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group. Examples thereof include: trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl groups.

As the "trialkylsilyl group", there may be mentioned groups in which three hydrogens of the silyl group are each independently substituted with an alkyl group, and the alkyl group may refer to the group described as the "alkyl group" in the first substituent. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples thereof include: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-pentyl, and the like.

Specific examples of the trialkylsilyl group include: trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, tri-sec-butylsilyl group, tri-tert-pentylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl group, tert-pentyldimethylsilyl group, methyldiethylsilyl group, propyldiethylsilyl group, isopropyldiethylsilyl group, butyldiethylsilyl group, sec-butyldiethylsilyl group, tert-butyldiethylsilyl group, methyldipropylsilyl group, ethyldipropylsilyl group, butyldipropylsilyl group, sec-butyldipropylsilyl group, tert-pentyldipropylsilyl group, methyldiisopropylsilyl group, methyl-propylsilyl group, ethyl-dimethylsilyl group, tert-butyldimethylsilyl group, tert-butyldipropylsilyl group, tert-butyldimethylsilyl group, tert-pentyldipropylsilyl group, methyl-butyldi-butylsilyl group, methyl-butyldimethylsilyl group, a, Ethyldiisopropylsilane, butyldiisopropylsilane, sec-butyldiisopropylsilane, tert-amyldiisopropylsilane, etc.

As the "tricycloalkylsilyl group", there can be cited groups in which three hydrogens in the silyl group are each independently substituted with a cycloalkyl group, and the cycloalkyl group can cite the group described as the "cycloalkyl group" in the first substituent. Preferred cycloalkyl groups for substitution are those having 5 to 10 carbon atoms, and specific examples thereof include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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, decahydronaphthyl, decahydroazulenyl, and the like.

Specific examples of the tricycloalkylsilyl group include tricyclopentylsilyl groups and tricyclohexylsilyl groups.

Specific examples of the dialkylcycloalkylsilyl group in which two alkyl groups are substituted with one cycloalkyl group and the alkylbicycloalkylsilyl group in which one alkyl group is substituted with two cycloalkyl groups include silyl groups in which a group selected from the specific alkyl groups and cycloalkyl groups is substituted.

Specific examples of the dialkylarylsilyl group in which two alkyl groups are substituted with one aryl group, the alkyldiarylsilyl group in which one alkyl group is substituted with two aryl groups, and the triarylsilyl group in which three aryl groups are substituted include silyl groups in which a group selected from the specific alkyl groups and aryl groups is substituted. Specific examples of the triarylsilyl group include triphenylsilyl groups.

In addition, "aryl" in "diarylboron group" as the first substituent may refer to the description of the aryl. In addition, the two aryl groups may be linked via a single bond or a linking group (e.g., > C (-R)₂A > O, > S, or > N-R) bond. Here, > C (-R)₂And R > N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl group (the above is the first substituent) in which aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group (the above is the second substituent) may be further substituted, and as specific examples of these groups, the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy as the first substituent may be cited.

Specifically, the emission wavelength can be adjusted by steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent, and is preferably a group represented by the following structural formula, more preferably a methyl group, a tert-butyl group, a tert-amyl (t-amyl) group, a tert-octyl group, a neopentyl group, a cyclohexyl group, an adamantyl group, a phenyl group, an o-tolyl group, a p-tolyl group, a 2, 4-xylyl group, a 2, 5-xylyl group, a 2, 6-xylyl group, a 2,4, 6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis (p-tert-butyl) phenyl group, a carbazolyl group, a 3, 6-dimethylcarbazolyl group, a 3, 6-di-tert-butylcarbazolyl group, and a phenoxy group, and further preferably a methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a neopentyl group, an adamantyl group, and a phenoxy group, Phenyl, o-tolyl, 2, 6-xylyl, 2,4, 6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (tert-butyl) phenyl) amino, carbazolyl, 3, 6-dimethylcarbazolyl, and 3, 6-di-tert-butylcarbazolyl. From the viewpoint of ease of synthesis, a group having a large steric hindrance is preferable for selective synthesis, and specifically, a tert-butyl group, a tert-amyl (t-amyl), a tert-octyl group, an adamantyl group, an o-tolyl group, a p-tolyl group, a 2, 4-xylyl group, a 2, 5-xylyl group, a 2, 6-xylyl group, a 2,4, 6-mesityl group, a di-p-tolylamino group, a bis (p- (tert-butyl) phenyl) amino group, a 3, 6-dimethylcarbazolyl group, and a 3, 6-di-tert-butylcarbazolyl group are preferable.

In the following structural formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-pentyl group, "thoct" represents a tert-octyl group, and a bond site.

[ solution 129]

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[ 138]

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In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d) and the formulaIn the formulae (2-e) and (2-f), R is preferably¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R ¹¹1 to 4 of the (a) are a group represented by any one of the structural formulae, and the remainder are hydrogen, more preferably R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R ¹¹1 to 3 of the (a) groups are a group represented by any one of the structural formulae, and the remainder is hydrogen, more preferably R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R ¹¹1 to 3 of these are methyl, tert-butyl or tert-pentyl, the remainder being hydrogen.

A substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryl groups may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", or a substituted or unsubstituted "aryloxy" as specified as substituted or unsubstituted, at least one of which may be substituted with a second substituent. Examples of the second substituent include an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, and a substituted silyl group, and specific examples thereof can be described with reference to the monovalent group of the "aryl ring" or the "heteroaryl ring" and the "alkyl group", "cycloalkyl group", or substituted silyl group as the first substituent. In addition, among the aryl or heteroaryl groups as the second substituent, a structure in which at least one hydrogen of them is substituted with an aryl group such as a phenyl group (specifically, the above-mentioned group), an alkyl group such as a methyl group (specifically, the above-mentioned group), or a cycloalkyl group such as a cyclohexyl group (specifically, the above-mentioned group) is also included in the aryl or heteroaryl groups as the second substituent. For example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl group such as a phenyl group, an alkyl group such as a methyl group, or a cycloalkyl group such as a cyclohexyl group is also included in the heteroaryl group as the second substituent.

R as formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) and formula (2-f)¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹The aryl, heteroaryl, diarylamino aryl, diheteroarylamino heteroaryl, arylheteroarylamino aryl and heteroaryl, diarylboron aryl or aryloxy aryl group in (1) may be exemplified by a monovalent group of the "aryl ring" or "heteroaryl ring" illustrated in formula (2). In addition, as R¹～R¹¹The alkyl group, cycloalkyl group or alkoxy group in (1) can be referred to the description of "alkyl", "cycloalkyl" or "alkoxy" as the first substituent in the description of the above formula (2). Further, aryl, heteroaryl, alkyl or cycloalkyl groups as substituents for these groups are also the same. In addition, as R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹The heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, or aryloxy groups as well as the aryl, heteroaryl, alkyl, or cycloalkyl groups as further substituents for the rings in the case where adjoining groups in (a) are bonded to each other and form an aryl or heteroaryl ring together with the a-, b-, or c-ring are also the same.

X of formula (2)¹And X²R > N-R in (A) is aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in the aryl or heteroaryl group may be substituted, for example, by alkyl, cycloalkyl or substituted silyl groups. As the aryl, heteroaryl, alkyl and cycloalkyl, the above-mentioned groups can be mentioned. Particularly preferably an aryl group having 6 to 10 carbon atoms (e.g., phenyl group, naphthyl group, etc.) A heteroaryl group having 2 to 15 carbon atoms (e.g., carbazolyl group), an alkyl group having 1 to 5 carbon atoms (e.g., methyl group, ethyl group, etc.), or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group). The same applies to X in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f)¹And X². X 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)¹And X²R > N-R in (1) is an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and preferably an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

X of formula (2)¹And X²Middle > C (-R)₂R of (a) is hydrogen, aryl, alkyl or cycloalkyl, at least one hydrogen in the aryl group being substitutable, for example, by alkyl, cycloalkyl or substituted silyl groups. Examples of the aryl group, the alkyl group and the cycloalkyl group include the groups described above. Particularly preferred is an aryl group having 6 to 10 carbon atoms (e.g., phenyl group, naphthyl group, etc.), an alkyl group having 1 to 5 carbon atoms (e.g., methyl group, ethyl group, etc.), or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group). The same applies to X in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f) ¹And X². X 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)¹And X²Middle > C (-R)₂R in (A) is hydrogen, an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and preferably hydrogen, an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

-C (-R) as a linking group in the formula (2)₂R of the above-mentioned group is hydrogen, an alkyl group or a cycloalkyl group, and the alkyl group and the cycloalkyl group may be the same groups as those mentioned above. Particularly preferably an alkyl group having 1 to 5 carbon atoms (for exampleSuch as methyl group, ethyl group, etc.), or a cycloalkyl group having 5 to 10 carbon atoms (preferably a cyclohexyl group or adamantyl group). The same applies to the linkage group 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) — C (-R)₂-”。

The dopant material may be a polymer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2). The polymer is preferably a polymer of a polycyclic aromatic compound having a plurality of unit structures 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). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be in a form having a plurality of unit structures as described above in one compound, and for example, in addition to a form in which a plurality of unit structures are bonded by a single bond, a linking group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, or the like, a form in which a plurality of unit structures are bonded so as to share an arbitrary ring (a ring, B ring, or C ring, a ring, B ring, or C ring) included in the unit structure, or a form in which an arbitrary ring (a ring, B ring, or C ring, a ring, B ring, or C ring) included in the unit structure is condensed with each other may be used.

Examples of such multimers include multimer compounds represented by the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4), or formula (2-6). The symbols in these formulae have the same meanings as in formula (2-a), and the preferable ranges are also the same. The multimeric compound represented by the following formula (2-4) is described as the multimeric compound represented by the formula (2-a), and is a multimeric compound having a plurality of unit structures represented by the formula (2-a) in one compound so as to share a benzene ring as an a-ring. In addition, the following formula (2-4-1) expressed polymer compounds are described as the type (2-a), in a way of sharing a benzene ring as a ring, in a compound with two formula (2-a) expressed unit structure polymer compounds. In addition, the following formula (2-4-2) expressed polymer compounds are described as the type (2-a), in a way of sharing a ring as a benzene ring, in a compound with three formula (2-a) expressed unit structure polymer compounds. In addition, the following formula (2-5-1) -formula (2-5-4) expressed polymer compounds described in the formula (2-a), so as to share as b ring (or c ring) benzene ring, in a compound with a plurality of formula (2) unit structure polymer compounds. In addition, the following formula (2-6) expressed polymer compounds are described as the formula (2-a), for example, a unit structure of b ring (or a ring, C ring) benzene ring and a unit structure of b ring (or a ring, C ring) benzene ring condensation, in a compound having a plurality of type (2-a) unit structure of polymer compounds.

[ solution 142]

The polymer compound may be a polymer in which the polymerization form expressed by the formula (2-4), the formula (2-4-1), or the formula (2-4-2) and the polymerization form expressed by any one of the formulae (2-5-1) to (2-5-4), or the formula (2-6) are combined, a polymer in which the polymerization form expressed by any one of the formulae (2-5-1) to (2-5-4) and the polymerization form expressed by the formula (2-6) are combined, or a polymer in which the polymerization form expressed by the formula (2-4), the formula (2-4-1), or the formula (2-4-2) and the polymerization form expressed by any one of the formulae (2-5-1) to (2-5-4) and the polymerization form expressed by the formula (2-6) are combined And (3) a body.

Further, all or a part of hydrogen in the chemical structure of the polycyclic aromatic compound represented by 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) and the multimer thereof may be deuterium, cyano or halogen. For example, in formula (2), ring A, ring B, ring C (ring A to ring C are aryl or heteroaryl rings), substituents for ring A to ring C, and X³And X⁴Is > N-R or > C (-R)₂In the case of R (═ alkyl, cycloalkyl, and aryl), hydrogen may be substituted with deuterium, cyano, or halogen, and among these, all or part of hydrogen in aryl or heteroaryl may be substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, Bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

In addition, at least one selected from the group consisting of an aryl ring and a heteroaryl ring in the chemical structures of the polycyclic aromatic compound represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) and the multimer thereof may be condensed with at least one cycloalkane.

For example, an aryl ring and a heteroaryl ring in an aryl ring and a heteroaryl ring as the a ring, the B ring, the C ring, an aryl group (an aryl moiety in an aryl group, diarylamino group, arylheteroarylamino group, diarylboron group, or aryloxy group) and a heteroaryl group (a heteroaryl moiety in a heteroaryl group, diheteroarylamino group, or arylheteroarylamino group) as the first substituent and the second substituent in the a ring to the C ring, an aryl group (the same as those described) and a heteroaryl group (the same as those described above) as the first substituent and the second substituent to the a ring, the B ring, the C ring, and the like as the substituents to be X¹、X²Is greater than N-R and greater than C (-R)₂At least one of the aryl (same as described) and heteroaryl (same as described) of R (A) may be condensed with at least one cycloalkane.

Preferably, the aryl ring and heteroaryl ring as ring A, ring B, ring C, ring a, ring B and ring C, the aryl (aryl moiety in aryl, diarylamino, diarylboron or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents in ring A to ring C, the aryl (same as described above) and heteroaryl (same as described above) as the first substituents in ring a to ring C, and the heteroaryl (same as described above) as the substituent X ¹、X²Is greater than N-R and greater than C (-R)₂At least one of the aryl (same as described) and heteroaryl (same as described) of R (A) may be condensed with at least one cycloalkane.

More preferably, the aryl ring of ring A, ring B, ring C, ring a, ring B and ring C, the aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents in ring A to ring C, the aryl (same as described above) and heteroaryl (same as described above) as the first substituents for ring a, ring B and ring C, and the heteroaryl (same as described above) as the first substituents for ring a, ring B and ring CIs formed as X¹、X²Is greater than N-R and greater than C (-R)₂At least one of the aryl groups (same as described) of R (a) may be condensed with at least one cycloalkane.

Further preferred are aryl rings of ring A, ring B, ring C, ring a, ring B and ring C, aryl (aryl group or aryl moiety in diarylamino group) as a first substituent in ring A to ring C, aryl (the same as described above) as a first substituent for ring a, ring B and ring C, and aryl as a first substituent for ring X¹、X²Is greater than N-R and greater than C (-R)₂At least one of the aryl groups (same as described) of R (a) may be condensed with at least one cycloalkane.

Examples of the "cycloalkane" include: a C3-24 cycloalkane, a C3-20 cycloalkane, a C3-16 cycloalkane, a C3-14 cycloalkane, a C5-10 cycloalkane, a C5-8 cycloalkane, a C5-6 cycloalkane, a C5 cycloalkane, and the like.

Specific examples of the cycloalkane include: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane, bicyclo [1.0.1] butane, bicyclo [1.1.1] pentane, 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, adamantane, bisadamantane, decahydronaphthalene, and decahydroazulene, and alkyl (particularly methyl) substituents, halogen (particularly fluorine) substituents, deuterium substituents having 1 to 5 carbon atoms thereof, and the like.

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

Particularly preferred is a structure in which a partial structure represented by the following formula (B10) or formula (B11) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring.

[ solution 143]

In the formulae (B10) and (B11), Me represents a methyl group. Represents a bonding position, and the group represented by formula (B10) or formula (B11) is bonded to two elements adjacent to each other on the ring of the bonded aryl or heteroaryl ring, respectively.

Examples of the compound having such a structure include the following compounds.

[ solution 144]

The number of cycloalkanes condensed into one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1. For example, examples in which one or more cycloalkanes are condensed on one benzene ring (phenyl group) are shown below. The condensed cycloalkanes may be condensed with each other as shown in the formulae (Cy-1-4) and (Cy-2-4). The same applies to the case where the condensed ring (group) is an aromatic ring or a heteroaromatic ring other than a benzene ring (phenyl group), and the case where the cycloalkane to be condensed is cyclopentane or a cycloalkane other than cyclohexane.

[ solution 145]

At least one-CH in cycloalkanes₂-may be substituted by-O-. For example, the following shows one or more-CH condensed in cycloalkane of one benzene ring (phenyl group)₂Examples of substitution by-O-. The same applies to the case where the condensed ring (group) is an aromatic ring or a heteroaromatic ring other than a benzene ring (phenyl group), and the case where the cycloalkane to be condensed is cyclopentane or a cycloalkane other than cyclohexane.

[ solution 146]

At least one hydrogen in the cycloalkane may be substituted, and as the substituent, for example: aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, the details of which may be cited in the description of the first substituent. Among these substituents, preferred are alkyl groups (e.g., alkyl groups having 1 to 6 carbon atoms), cycloalkyl groups (e.g., cycloalkyl groups having 3 to 14 carbon atoms), halogens (e.g., fluorine), and deuterium. When the cycloalkyl group is substituted, the substituted form may be a spiro structure, and the examples are shown below.

[ solution 147]

Other forms of the cycloalkane condensation include: the polycyclic aromatic compound represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) and multimers thereof have examples such as R > N-R which is an aryl group condensed by cycloalkane, diarylamino group condensed by cycloalkane (condensed to its aryl moiety), carbazolyl group condensed by cycloalkane (condensed to its benzene ring moiety) or benzocarbazolyl group condensed by cycloalkane (condensed to its benzene ring moiety). As the "diarylamino group", the groups described as the "first substituent" can be mentioned.

Further, as more specific examples, there are: r in the polycyclic aromatic 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) and a multimer thereof²Are examples of diarylamino groups (condensed to the aryl portion thereof) condensed from cycloalkane or carbazolyl groups (condensed to the benzene ring portion thereof) condensed from cycloalkane.

More specific examples of the polycyclic aromatic compound represented by the formula (2) include compounds represented by the following formulae. In the following formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "iPr" represents an isopropyl group, "Ph" represents a phenyl group, "tAm" represents a tert-pentyl group (tertiary pentyl), and "D" represents deuterium.

[ solution 148]

[ 149]

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[ chemical formula 157]

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[ solution 183]

[ solution 184]

[ solution 185]

[ solution 186]

[ solution 187]

[ solution 188]

[ formulation 189]

[ solution 190]

1-2-2 polycyclic aromatic Compound represented by formula (2) and method for producing multimer thereof

The polycyclic aromatic compound represented by the formula (2) and the multimer thereof can be synthesized, for example, by the method disclosed in international publication No. 2019/009052 as "method for producing the polycyclic aromatic compound represented by the formula (2) and the multimer thereof".

1-3. luminescent layer

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

The dopant material may be contained within the bulk of the host material, or may be contained within a portion of the host material, either. The doping method may be a co-evaporation method with the host material, or may be a method in which the host material is mixed in advance and then evaporated at the same time.

The amount of the host material to be used differs depending on the type of the host material, and may be determined in accordance with the characteristics of the host material. The amount of the host material used is preferably 50 to 99.999 mass%, more preferably 80 to 99.95 mass%, and still more preferably 90 to 99.9 mass% of the total of the light-emitting layer material.

The amount of the dopant material used differs depending on the type of the dopant material, and may be determined by matching the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass of the entire material for the light-emitting layer. In the above range, for example, concentration quenching is preferably prevented.

Examples of the host material that can be used in combination with the compound represented by formula (1) include: pyrene and dibenzo known as luminophors since before

Fused ring derivatives such as stilbene anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

As a dopant material that can be used in combination with the compound represented by formula (2), there can be mentioned: fused ring derivatives such as anthracene and pyrene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives, which have been known as light emitters.

2. Electron injection layer and electron transport layer of organic electroluminescent element

The electron injection layer 107 functions to efficiently inject electrons transferred from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 functions to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light-emitting layer 105. The electron transporting layer 106 and the electron injecting layer 107 are formed by laminating and mixing one or more kinds of electron transporting/injecting materials, or are formed by mixing an electron transporting/injecting material and a polymer binder.

The electron injection/transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons, and it is desirable that the injected electrons be efficiently transported with high electron injection efficiency. Therefore, a substance having a high electron affinity, a high electron mobility, and excellent stability is preferable, and impurities that become traps are less likely to be generated during production and use. However, when the balance between the transport of holes and electrons is considered, if the effect of efficiently preventing holes from the anode from flowing to the cathode side without being recombined is mainly exerted, the effect of improving the light emission efficiency is obtained as in the case of a material having a high electron transport ability even if the electron transport ability is not so high. Therefore, the electron injection/transport layer in this embodiment mode may also have a function of a layer which can efficiently prevent the transfer of holes.

The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be selected and used as desired from compounds conventionally used as electron transport compounds in photoconductive materials, and conventional compounds used in electron injection layers and electron transport layers of organic EL devices.

The material used for the electron transport layer or the electron injection layer preferably contains at least one compound selected from the following compounds: a compound containing an aromatic ring or a heteroaromatic ring containing at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and fused ring derivatives thereof; and a metal complex having electron-accepting nitrogen. Specifically, there may be mentioned: fused ring aromatic ring derivatives such as naphthalene and anthracene, styrene aromatic ring derivatives represented by 4,4' -bis (diphenylvinyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include: and hydroxyoxazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials may be used alone or in combination with different materials.

Specific examples of the other electron transport compound include: borane derivatives, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1, 3-bis [ (4-tert-butylphenyl) 1,3, 4-oxadiazolyl ] phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2, 5-diphenyl-1, 3, 4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline (oxine) derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, indole (benzazole) compounds, gallium complexes, fluorine complexes, etc, Pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (e.g., 2 '-bis (benzo [ h ] quinolin-2-yl) -9,9' -spirobifluorene), imidazopyridine derivatives, benzimidazole derivatives (e.g., tris (N-phenylbenzimidazol-2-yl) benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine and other oligopyridine derivatives, bipyridine derivatives, terpyridine derivatives (e.g., 1, 3-bis (4'- (2, 2': 6 '2' -terpyridyl)) benzene), naphthyridine derivatives (e.g., bis (1-naphthyl) -4- (1, 8-naphthyridin-2-yl) phenylphosphine oxide, etc.), and the like, Aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, oxazoline derivatives, and the like.

In addition, a metal complex having electron-accepting nitrogen may also be used, and examples thereof include: hydroxyoxazole complexes such as hydroxyquinoline metal complexes and hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

The materials can be used alone or in admixture with different materials.

Among the above materials, preferred are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and oxazoline derivatives.

Borane derivatives

The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in Japanese patent laid-open No. 2007-27587.

[ solution 191]

In the formula (ETM-1), R¹¹And R¹²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R ¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, X is an arylene group which may be substituted, Y is an aryl group having 16 or less carbon atoms which may be substituted, a substituted boron group, or a substituted carbazolyl group, and n is each independently an integer of 0 to 3. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

Among the compounds represented by the formula (ETM-1), a compound represented by the following formula (ETM-1-1) or a compound represented by the following formula (ETM-1-2) is preferable.

[ solution 192]

In the formula (ETM-1-1), R¹¹And R¹²Independently of one another, hydrogen, alkyl, cycloalkyl, optionally substituted arylAt least one of a group, a substituted silyl group, a nitrogen-containing heterocycle which may be substituted or a cyano group, R¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, R²¹And R²²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, X¹Is an arylene group having 20 or less carbon atoms which may be substituted, n is independently an integer of 0 to 3, and m is independently an integer of 0 to 4. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

[ solution 193]

In the formula (ETM-1-2), R¹¹And R¹²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted or an aryl group which may be substituted, X¹Is an arylene group having 20 or less carbon atoms which may be substituted, and n is an integer of 0 to 3 independently. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

As X¹Specific examples of (2) include divalent groups represented by any one of the following formulae (X-1) to (X-9).

[ solution 194]

(in the formulae, R^aEach independently being an alkyl, cycloalkyl or optionally substituted phenyl group, representing a bonding position)

Specific examples of the borane derivative include the following compounds.

[ solution 195]

The borane derivatives can be produced using conventional starting materials and conventional synthesis methods.

< pyridine derivatives >

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

[ solution 196]

Phi 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 1-4.

In the formula (ETM-2-1), R¹¹～R¹⁸Each independently represents hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms) or an aryl group (preferably an aryl group having 6 to 30 carbon atoms).

In the formula (ETM-2-2), R¹¹And R¹²Each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl), R¹¹And R¹²May be bonded to form a ring.

In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15) (wherein:. represents a bonding site), and the pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like, and methyl is preferable. In addition, the pyridine substituent may be bonded to the phi, anthracene ring or fluorene ring in each formula via phenylene or naphthylene.

[ solution 197]

The pyridine substituent is any one of the formulae (Py-1) to (Py-15), and among these, any one of the formulae (Py-21) to (Py-44) (wherein:. represents a bonding site) is preferable.

[ chemical formula 198]

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

As R¹¹～R¹⁸The "alkyl group" in (1) may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms and a branched alkyl group having 3 to 24 carbon atoms. The preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms). More preferably, the "alkyl group" is an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms). Further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms). Particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms).

As the alkyl group having 1 to 4 carbon atoms substituted with a pyridine substituent, the description thereof can be cited.

As R¹¹～R¹⁸Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. The preferable "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms.

Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

As R¹¹～R¹⁸The "aryl group" in (1) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group having 6 to 30 carbon atoms" include: phenyl as monocyclic aryl; (1-, 2-) naphthyl as a condensed bicyclic aryl; acenaphthene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl as condensed tricyclic aryl; triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, tetracene- (1-, 2-, 5-) yl as condensed tetra-ring system aryl; perylene- (1-, 2-, 3-) group, pentacene- (1-, 2-, 5-, 6-) group, and the like as condensed five-ring system aryl group.

Preferred examples of the "aryl group having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl,

Examples of the group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group and a phenanthryl group, and examples of the group include a phenyl group, a 1-naphthyl group and a 2-naphthyl group.

R in the formula (ETM-2-2)¹¹And R¹²Can bond to form a ring, and as a result, cyclobutane can be spiro-bonded to the five-membered ring of the fluorene skeletonCyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like.

Specific examples of the pyridine derivative include the following compounds.

[ solution 199]

The pyridine derivative can be produced using a conventional raw material and a conventional 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.

[ solution 200]

In the formula (ETM-3), X¹²～X²¹Represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, as the substituent in the case of substitution, there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

Specific examples of the fluoranthene derivative include the following compounds.

[ solution 201]

< BO series derivative >

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

[ solution 202]

R⁶¹～R⁷¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, at least one of which may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

In addition, R⁶¹～R⁷¹May be bonded to each other and together with the a-ring, b-ring or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the formed ring may be substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, at least one of which may be substituted by aryl, heteroaryl, alkyl or cycloalkyl.

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

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

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

[ solution 203]

The BO-based derivative can be produced using a conventional raw material and a conventional synthesis method.

< Anthracene derivatives >

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

[ 204]

Ar¹Each independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene or phenalene.

Ar²Each independently an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples of the "aryl group having 6 to 20 carbon atoms" include: phenyl, (o, m, p) tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-) xylyl, mesityl (2,4, 6-trimethylphenyl), (o, m, p) cumenyl, which is a monocyclic aryl group; (2-, 3-, 4-) biphenyl as a bicyclic aryl group; (1-, 2-) naphthyl as a condensed bicyclic aryl; terphenyl groups (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) as tricyclic aryl groups; anthracene- (1-, 2-, 9-) radical, acenaphthene- (1-, 3-, 4-, 5-) radical, fluorene- (1-, 2-, 3-, 4-, 9-) radical, phenalene- (1-, 2-) radical, (1-, 2-, 3-, 4-, 9-) phenanthrene radical as condensed tricyclic aryl radicals; triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, tetracene- (1-, 2-, 5-) yl as condensed tetra-ring system aryl; perylene- (1-, 2-, 3-) groups as condensed five-ring system aryl groups, and the like. Specific examples of the "aryl group having 6 to 10 carbon atoms" include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

R¹～R⁴Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms.

With respect to R¹～R⁴The alkyl group having 1 to 6 carbon atoms in the group may be either a straight chain or a branched chain. Namely, a C1-6 linear alkyl group or a C3-6 branched alkyl group. More preferably an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms). Specific examples thereof include: methyl, ethyl, n-butylPropyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, or 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, or tert-butyl.

As R¹～R⁴Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in (b) include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

With respect to R¹～R⁴The aryl group having 6 to 20 carbon atoms in (A) is preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. As a specific example of "aryl group having 6 to 20 carbon atoms", Ar ²Specific examples of the "aryl group having 6 to 20 carbon atoms" in (1). The "aryl group having 6 to 20 carbon atoms" is preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group or an m-terphenyl-5' -yl group, further preferably a phenyl group, a biphenyl group, a 1-naphthyl group or a 2-naphthyl group, and most preferably a phenyl group.

Specific examples of the anthracene derivative include the following compounds.

[ formulation 205]

These anthracene derivatives can be produced using conventional raw materials and conventional synthesis methods.

< benzofluorene derivative >

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

[ solution 206]

Ar¹Each independently an aryl group having 6 to 20 carbon atoms, and Ar of the formula (ETM-5)²The "aryl group having 6 to 20 carbon atoms" in (A) is the same as defined above. Preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples thereof include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

Ar²Independently represents hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl), or two Ar ²May be bonded to form a ring.

As Ar²The "alkyl group" in (1) may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms and a branched alkyl group having 3 to 24 carbon atoms. The preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms). More preferably, the "alkyl group" is an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms). Further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms). Particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms). Specific examples of the "alkyl group" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

As Ar²Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. The preferable "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms. Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

As Ar²The "aryl group" of (1) "The aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group having 6 to 30 carbon atoms" include: phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, pentacenyl, and the like.

Two Ar²The bond may form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to a five-membered ring of the fluorene skeleton.

Specific examples of the benzofluorene derivative include the following compounds.

[ solution 207]

The benzofluorene derivative can be produced using conventional raw materials and conventional synthesis methods.

< 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 international publication No. 2013/079217 and international publication No. 2013/079678.

[ solution 208]

R⁵Is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R⁶CN, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 16 carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group having 5 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms or aryloxy group having 6 to 20 carbon atoms,

R⁷and R⁸Each independently is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms, R⁹Is oxygen or sulfur, and is selected from the group consisting of,

j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.

Here, as the substituent in the case of substitution, there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

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

[ solution 209]

R¹～R³Which may be the same or different, is selected from the group consisting of hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, arylthioether, aryl, heterocyclic, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and fused rings formed between adjacent substituents.

Ar¹May be the same or different and is an arylene or heteroarylene group. Ar (Ar)²May be the same or different and is aryl or heteroaryl. Wherein Ar is ¹And Ar²Has a substituent, or forms a condensed ring with an adjacent substituent. n is an integer of 0 to 3, and when n is 0, no unsaturated moiety is present, and when n is 3, no R is present¹。

Among these substituents, the alkyl group means, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, and the alkyl group may be unsubstituted or substituted. The substituent in the case of substitution is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group, and these are also common in the following description. The number of carbons of the alkyl group is not particularly limited, and is usually in the range of 1 to 20 in terms of easiness of obtaining and cost.

The cycloalkyl group means a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group and the like, and the cycloalkyl group may be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, and is usually within a range of 3 to 20.

The aralkyl group means an aromatic hydrocarbon group such as a benzyl group or a phenylethyl group through which an aliphatic hydrocarbon is interposed, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, and is usually in the range of 1 to 20.

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

The cycloalkenyl group means an unsaturated alicyclic hydrocarbon group having a double bond, such as cyclopentenyl group, cyclopentadienyl group, and cyclohexene, and the cycloalkenyl group may be unsubstituted or substituted.

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

The alkoxy group means, for example, an aliphatic hydrocarbon group such as a methoxy group through an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms of the alkoxy group is not particularly limited, and is usually in the range of 1 to 20.

The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.

The cycloalkylthio group is a group in which an oxygen atom of an ether bond of a cycloalkoxy group is substituted with a sulfur atom.

The aryl ether group means an aromatic hydrocarbon group such as a phenoxy group through an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms of the aryl ether group is not particularly limited, and is usually in the range of 6 to 40.

The arylthioether group is a group in which an oxygen atom of an ether bond of an arylether group is substituted with a sulfur atom.

The aryl group represents, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbons of the aryl group is not particularly limited, and is usually in the range of 6 to 40.

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

Halogen means fluorine, chlorine, bromine and iodine.

The formyl group, the carbonyl group, and the amino group may further include a group substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle, or the like.

Further, the aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocyclic ring may be unsubstituted or substituted.

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

The condensed ring formed between the adjacent substituent is, for example, Ar¹And R²、Ar¹And R³、Ar²And R²、Ar²And R³、R²And R³、Ar¹And Ar²Etc. are formed between them. Here, in the case where n is 1, two R' s¹May form conjugated or non-conjugated fused rings with each other. These condensed rings may contain a nitrogen atom, an oxygen atom, a sulfur atom in the ring inner structure, or may be further condensed with other rings.

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

[ solution 210]

The phosphine oxide derivatives can be produced using existing starting materials and existing synthetic methods.

[ pyrimidine derivative ]

The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in international publication No. 2011/021689.

[ solution 211]

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

Examples of the "aryl group" of the "aryl group which may be substituted" include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and still more preferably aryl groups having 6 to 12 carbon atoms.

Specific "aryl" groups include: phenyl as monocyclic aryl; (2-, 3-, 4-) biphenyl as a bicyclic aryl group; (1-, 2-) naphthyl as a condensed bicyclic aryl; terphenyl groups (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) as tricyclic aryl groups; acenaphthene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl as condensed tricyclic aryl; tetrabiphenyl group (5' -phenyl-m-terphenyl-2-yl, 5' -phenyl-m-terphenyl-3-yl, 5' -phenyl-m-terphenyl-4-yl, m-quaterphenyl) as a tetracyclic aryl group; triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, tetracene- (1-, 2-, 5-) yl as condensed tetra-ring system aryl; perylene- (1-, 2-, 3-) group, pentacene- (1-, 2-, 5-, 6-) group, and the like as condensed five-ring system aryl group.

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

Specific examples of the heteroaryl group include: furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo [ b ] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathinyl, thianthrenyl, indolizinyl and the like.

Additionally, the aryl and heteroaryl groups may be substituted, such as by the aryl or heteroaryl groups, respectively.

Specific examples of the pyrimidine derivative include the following compounds.

[ solution 212]

The pyrimidine derivative can be produced using conventional starting materials and conventional synthetic methods.

< aryl nitrile derivatives >

The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer thereof in which a plurality of arylnitrile derivatives are bonded by a single bond or the like. Details are described in U.S. application publication No. 2014/0197386.

[ solution 213]

From the viewpoint of fast electron-transporting property, Ar_niPreferably a large number of carbon atoms, and Ar is Ar from the viewpoint of a high T1_niPreferably, the number of carbon atoms is small. Specifically, it is preferable that T1 is high and Ar is high when used for a layer adjacent to the light-emitting layer_niThe aryl group has 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms. The number n of nitrile groups substituted is preferably large from the viewpoint of high T1, and preferably small from the viewpoint of high S1. Specifically, the number n of substitution of nitrile groups is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and still more preferably 1.

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. From the viewpoint of high S1 and high T1, donor heteroaryl groups are preferable, and since they are used as an electron transport layer, donor heteroaryl groups are preferably small. From the viewpoint of charge transport properties, aryl or heteroaryl groups having a large number of carbon atoms are preferable, and a large number of substituents are preferable. Specifically, the number m of substitution of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

Specific "aryl" groups include: phenyl as a monocyclic aryl group, (2-, 3-, 4-) biphenyl as a bicyclic aryl group, (1-, 2-) naphthyl as a condensed bicyclic aryl group, (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-1-2-naphthyl as a tricyclic aryl group, terphenyl-4 ' -yl as a tricyclic aryl group, P-terphenyl-4-yl), acenaphthylene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) based, phenalene- (1-, 2-) based, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetrabiphenyl (5' -phenyl-m-terphenyl-2-yl, 5' -phenyl-m-terphenyl-3-yl, 5' -phenyl-m-terphenyl-4-yl, m-quaterphenyl) as tetracyclic aryl, triphenylene- (1-, 2-) based as condensed tetracyclic aryl, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group, perylene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, pentacene- (1-, 2-, 5-, 6-) group, and the like.

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

Specific examples of the arylnitrile derivative include the following compounds.

[ solution 214]

The aryl nitrile derivative can be produced using conventional starting materials and conventional synthesis methods.

< triazine derivative >

The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Details are described in U.S. application publication No. 2011/0156013.

[ solution 215]

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

Specific examples of the triazine derivative include the following compounds.

[ 216]

The triazine derivative can be produced using a conventional raw material and a conventional synthesis method.

< benzimidazole derivative >

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

[ solution 217]

Phi- (benzimidazole substituent) n (ETM-11)

Phi 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), n is an integer of 1 to 4, the "benzimidazole substituent" is a substituent in which a pyridyl group in the "pyridine substituent" of the formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is substituted with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium.

[ solution 218]

Denotes a bonding site.

R in said benzimidazolyl group¹¹Hydrogen, alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms or aryl group having 6 to 30 carbon atoms, R in the formulae (ETM-2-1) and (ETM-2-2)¹¹And (4) description.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in that case can be referred to the description in the formula (ETM-2-1) or the formula (ETM-2-2), R in each formula ¹¹～R¹⁸Reference may be made to the description in formula (ETM-2-1) or formula (ETM-2-2). In addition, although the formula (ETM-2-1) or the formula (ETM-2-2) has been described as the form in which two pyridine substituents are bonded, when these are substituted with benzimidazole substituents, two pyridine substituents may be substituted with benzimidazole substituents (that is, n ═ 2), or any one pyridine substituent may be substituted with benzimidazole substituents and R may be substituted with benzimidazole substituents¹¹～R¹⁸Substituted with another pyridine substituent (i.e., n ═ 1). Further, R in the formula (ETM-2-1) may be substituted with a benzimidazole substituent¹¹～R¹⁸And R is¹¹～R¹⁸Substituted "pyridine-based substituents".

Specific examples of the benzimidazole derivative include: 1-phenyl-2- (4- (10-phenylanthren-9-yl) phenyl) -1H-benzo [ d ] imidazole, 2- (4- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole, 5- (10- (naphthalen-2-yl) anthracen-9-yl) -1, 2-diphenyl-1H-benzo [ d ] imidazole, 1- (4- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -2-phenyl-1H-imidazole H-benzo [ d ] imidazole, 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole, 1- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -2-phenyl-1H-benzo [ d ] imidazole, 5- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) -1, 2-diphenyl-1H-benzo [ d ] imidazole, and the like.

[ solution 219]

The benzimidazole derivative can be produced using conventional raw materials and conventional synthetic methods.

[ 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.

[ solution 220]

Of the formulae R¹¹～R¹⁸Independently represents hydrogen or alkyl (preferably having carbon number of 1 to c)24 alkyl group), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms). Further, in the formula (ETM-12-1), R¹¹～R¹⁸Any of these bonds to φ as an aryl ring.

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

As R¹¹～R¹⁸The alkyl, cycloalkyl and aryl in (1) can refer to R in the formula (ETM-2)¹¹～R¹⁸And (4) description. Further, phi may be represented by the following structural formula in addition to the above examples. In the following structural formulae, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or terphenyl, and represents a bonding position.

[ solution 221]

Specific examples of the phenanthroline derivative include: 4, 7-diphenyl-1, 10-phenanthroline, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline, 9, 10-bis (1, 10-phenanthroline-2-yl) anthracene, 2, 6-bis (1, 10-phenanthroline-5-yl) pyridine, 1,3, 5-tris (1, 10-phenanthroline-5-yl) benzene, 9,9' -difluoro-bis (1, 10-phenanthrolin-5-yl), 2, 9-dimethyl-4, 7-biphenyl-1, 10-phenanthroline (bathocuproine), 1, 3-bis (2-phenyl-1, 10-phenanthrolin-9-yl) benzene, or a compound represented by the following structural formula.

[ solution 222]

The phenanthroline derivative can be produced using a conventional raw material and a conventional synthesis method.

< hydroxyquinoline-based metal complex >

The hydroxyquinoline metal complex is, for example, a compound represented by the following formula (ETM-13).

[ solution 223]

In the formula, R¹～R⁶Each independently is hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, M is Li, Al, Ga, Be or Zn, and n is an integer of 1 to 3.

Specific examples of the hydroxyquinoline metal complex include: lithium 8-quinolinolate, aluminum tris (8-quinolinolate), aluminum tris (4-methyl-8-quinolinolate), aluminum tris (5-methyl-8-quinolinolate), aluminum tris (3, 4-dimethyl-8-quinolinolate), aluminum tris (4, 5-dimethyl-8-quinolinolate), aluminum tris (4, 6-dimethyl-8-quinolinolate), aluminum bis (2-methyl-8-quinolinolate) (phenoxide), aluminum bis (2-methyl-8-quinolinolate) (2-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (3-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (4-methylphenol), aluminum tris (4-methyl-8-quinolinolate), Bis (2-methyl-8-quinolinolato) (2-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 3-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 6-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 4-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 5-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 5-di-tert-butylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 6-diphenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2,4, 6-triphenylpheno) aluminum, bis (2-methyl-8-quinolinolato) (2,4, 6-trimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2,4,5, 6-tetramethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, bis (2-methyl-8-quinolinolato) (2-naphthol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (2-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (4-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3, 5-dimethylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3, 5-di-tert-butylphenol) aluminum, bis (2-methyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2, 4-dimethyl-8-quinolinolato) aluminum- μ -oxo-bis (2, 4-dimethyl-8-quinolinolato) aluminum, aluminum, Bis (2-methyl-4-ethyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum -hydroxyquinoline) aluminum, bis (10-hydroxybenzo [ h ] quinoline) beryllium, and the like.

The hydroxyquinoline metal complex can be produced using a conventional raw material and a conventional synthesis method.

< thiazole derivatives and benzothiazole derivatives >

Examples of the thiazole derivative include compounds represented by the following formula (ETM-14-1).

[ 224]

Phi- (thiazole substituent) n (ETM-14-1)

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

[ solution 225]

Phi- (benzothiazole substituent) n (ETM-14-2)

Phi 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), n is an integer of 1 to 4, and a "thiazole substituent" or a "benzothiadiazole substituent" is a substituent in which a pyridyl group in the "pyridine substituent" of the formula (ETM-2), the formula (ETM-2-1) or the formula (ETM-2-2) is substituted with a thiazolyl group or a benzothiazolyl group as described below, and at least one of the thiazole derivative and the benzothiazole derivative may be substituted with deuterium.

[ chemical 226]

Denotes a bonding site.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in that case can be cited as in formula (ETM-2-1) or formula (ETM-2-2), eachIn the formula¹¹～R¹⁸Reference may be made to the description in formula (ETM-2-1) or formula (ETM-2-2). In addition, although the formula (ETM-2-1) or the formula (ETM-2-2) has been described as the form in which two pyridine substituents are bonded, when these are substituted with a thiazole substituent (or a benzothiazole substituent), two pyridine substituents (that is, n ═ 2) may be substituted with a thiazole substituent (or a benzothiazole substituent), or any one pyridine substituent may be substituted with a thiazole substituent (or a benzothiazole substituent) and R may be substituted with a thiazole substituent (or a benzothiazole substituent) ¹¹～R¹⁸Substituted with another pyridine substituent (i.e., n ═ 1). Further, R in the formula (ETM-2-1) may be substituted with, for example, a thiazole-based substituent (or a benzothiazole-based substituent)¹¹～R¹⁸And R is¹¹～R¹⁸Substituted "pyridine-based substituents".

These thiazole derivatives or benzothiazole derivatives can be produced using conventional starting materials and conventional synthetic methods.

Silole derivatives

Examples of the silole derivative include compounds represented by the following formula (ETM-15). The details are described in Japanese patent laid-open No. 9-194487.

[ formulation 227]

X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, which may be substituted. As for the details of these groups, the descriptions in the formulae (1) and (2) and the description in the formula (ETM-7-2) can be cited. Further, alkenyloxy and alkynyloxy are each a group in which an alkyl moiety in an alkoxy group is substituted with an alkenyl group or an alkynyl group, and the details of these alkenyl group and alkynyl group can be referred to the description in the formula (ETM-7-2).

In addition, X and Y may be bonded to form a cycloalkyl ring (a ring in which a part thereof becomes unsaturated), and details of the cycloalkyl ring can be referred to the description of the cycloalkyl group in the formulae (1) and (2).

R¹～R⁴Each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, mercapto, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isocyanate or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, or may form a fused ring with an adjacent substituent.

With respect to R¹～R⁴The halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in (1) and (2) can be cited as detailed in the description.

With respect to R¹～R⁴In the above (1), the alkyl, aryl and alkoxy groups in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy groups can be mentioned in detail as well as the descriptions in the formulae (1) and (2).

As the silane group, an unsubstituted silane group and a group in which at least one of the three hydrogens of the silane group is independently substituted with an aryl group, an alkyl group or a cycloalkyl group, are cited, and a ternary substituted silane group is preferable, and: triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, and the like. As for details of the aryl group, the alkyl group and the cycloalkyl group, the descriptions in the formula (1) and the formula (2) can be cited.

The condensed ring formed between the adjacent substituent is, for example, R¹And R²、R²And R³、R³And R⁴Etc. are formed between them. These condensed rings may contain a nitrogen atom, an oxygen atom, a sulfur atom in the ring inner structure, or may be further condensed with other rings.

Among them, the compound is preferably represented by the formula R¹And R⁴In the case of phenyl, X and Y are not alkyl or phenyl. In addition, it is preferable that R is not satisfied simultaneously¹And R⁴When it is thienyl, X and Y are alkyl and R²And R³Is alkyl, aryl, alkenyl or R²And R³A cycloalkyl group bonded to form a ring. In addition, it is preferable that when R is¹And R⁴When it is a silane group, R²、R³X and Y are each independently not hydrogen or alkyl of 1 to 6 carbon atoms. In addition, it is preferable that when R is in ¹And R²When a benzene ring is condensed on the above-mentioned group, X and Y are not an alkyl group or a phenyl group.

These silole derivatives can be produced using conventional starting materials and conventional synthetic methods.

< oxazoline derivative >

The oxazoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in international publication No. 2017/014226.

[ solution 228]

In the formula (ETM-16),

phi 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, at least one hydrogen of phi is substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 2 to 18 carbon atoms,

y is-O-, -S-or > N-Ar, Ar is aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, at least one hydrogen of Ar is substituted by alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, R is¹～R⁵Each independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein Ar in the above-mentioned formula > N-Ar and R are¹～R⁵Any one of which is a site bonded to L,

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),

[ solution 229]

In the formula (L-1), X¹～X⁶Each independently is ═ CR⁶-or ═ N-, X¹～X⁶At least two of which are ═ CR⁶-，X¹～X⁶Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR⁶R in (A-C)⁶Is a hydrogen atom, and is,

in the formula (L-2), X⁷～X¹⁴Each independently is ═ CR⁶-or ═ N-, X⁷～X¹⁴At least two of which are ═ CR⁶-，X⁷～X¹⁴Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR⁶R in (A-C)⁶Is a hydrogen atom, and is,

at least one hydrogen of L is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group 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 oxazoline ring and L may be the same or different, and,

at least one hydrogen in the compound represented by formula (ETM-16) may be substituted with deuterium.

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

[ solution 230]

In the formulae (ETM-16-1) and (ETM-16-2),

In the formula (ETM-16-1), Y is-O-, -S-or > N-Ar, Ar is aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, at least one hydrogen of Ar is substituted by alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms,

in the formula (ETM-16-1), R¹～R⁴Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Are the same, and R³And R⁴In the same way, the first and second,

in the formula (ETM-16-2), R¹～R⁵Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Are the same, and R³And R⁴In the same way, the first and second,

in the formulae (ETM-16-1) and (ETM-16-2),

[ solution 231]

in the formula (L-2), X⁷～X¹⁴Each independently is ═ CR⁶-or ═ N-, X⁷～X¹⁴At least two of which are ═ CR⁶-，X⁷～X¹⁴Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR ⁶R in (A-C)⁶Is a hydrogen atom, and is,

at least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

Preferably: and phi is selected from the group consisting of a monovalent group represented by the following formulas (phi 1-1) to (phi 1-18), a divalent group represented by the following formulas (phi 2-1) to (phi 2-34), a trivalent group represented by the following formulas (phi 3-1) to (phi 3-3), and a tetravalent group represented by the following formulas (phi 4-1) to (phi 4-2), wherein at least one hydrogen of phi is substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[ Hua 232]

[ 233]

[ solution 234]

Wherein Z is > CR²N-Ar, > N-L, -O-or-S-, > CR²Wherein R is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, R may be bonded to each other to form a ring, Ar in > N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, L in > N-L is a group represented by the formula (ETM-16) or (ETM) -16-1) or L in formula (ETM-16-2). Wherein denotes a bonding site.

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

Preferably: ar in > N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and pteridinyl, and at least one hydrogen of Ar in > N-Ar as Y is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.

Preferably: r¹～R⁴Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Same as R³And R⁴Are the same, and R¹～R⁴All of them do not simultaneously form hydrogen, and when m is 1 or 2, the group formed by the oxazoline ring and L is the same.

Specific examples of the oxazoline derivative include the following compounds. Further, "Me" in the structural formula represents a methyl group.

[ solution 235]

[ solution 236]

More preferably: φ is selected from the group consisting of divalent groups represented by the following formulae (2-1), (2-31), (2-32), (2-33) and (2-34), wherein at least one hydrogen of φ is substituted by an aryl group having 6 to 18 carbon atoms,

[ solution 237]

(indicates bonding position)

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine and triazine, at least one hydrogen of L is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 14 carbon atoms,

ar in > N-Ar as Y is selected from the group consisting of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl, wherein at least one hydrogen of Ar is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms,

R¹～R⁴each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Same as R³And R⁴Same, and no R is present¹～R⁴All of which are simultaneously in the case of hydrogen,

m is 2 and the group formed by the oxazoline ring and L is the same.

Other specific examples of the oxazoline derivative include the following compounds. Further, "Me" in the structural formula represents a methyl group.

[ solution 238]

With respect to details of the alkyl group, cycloalkyl group, aryl group or heteroaryl group in the formulae for specifying the oxazoline derivative, the descriptions in the formulae (1) and (2) may be cited.

The oxazoline derivative can be produced using an existing raw material and an existing synthesis method.

< reducing substance >

The electron transport layer or the electron injection layer may further include a substance that can reduce a material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain reducing property, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be preferably used.

Preferable reducing substances include Na (work function 2.36eV), K (work function 2.28eV), and R^bAn alkali metal such as (work function 2.16eV) or Cs (work function 1.95eV), or an alkaline earth metal such as Ca (work function 2.9eV), Sr (work function 2.0 to 2.5eV), or Ba (work function 2.52eV), and particularly preferably a substance having a work function of 2.9eV or less. Among these, K, R is the more preferable reducing substance ^bOr an alkali metal of Cs, more preferably R^bOr Cs, most preferably Cs. These alkali metals have particularly high reducing power, and by adding a relatively small amount of these alkali metals to a material forming the electron transporting layer or the electron injecting layer, improvement in light emission luminance or prolongation in life of the organic EL element can be achieved. In addition, as the reducing substance having a work function of 2.9eV or less, a combination of two or more of these alkali metals is also preferable, and a combination including Cs, such as Cs and Na, Cs and K, Cs and R, is particularly preferable^bOr Cs in combination with Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to a material for forming an electron transporting layer or an electron injecting layer, improvement in light emission luminance or prolongation in life of the organic EL element can be achieved.

3. Substrate for organic electroluminescent element

The substrate 101 serves as a support for the organic EL element 100, and quartz, glass, metal, plastic, or the like is generally used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape according to the purpose, and for example, a glass plate, a metal foil, a plastic film, a plastic sheet, or the like can be used. Among them, preferred are glass plates, polyesters, polymethacrylates, and polycarbonatesAnd a plate made of a transparent synthetic resin such as polysulfone. In the case of a glass substrate, soda-lime glass, alkali-free glass, or the like can be used, and the thickness is sufficient to maintain mechanical strength, and therefore, for example, it is sufficient if the thickness is 0.2mm or more. The upper limit of the thickness is, for example, 2mm or less, preferably 1mm or less. The material of the glass is preferably alkali-free glass because it is preferable that the amount of eluted ions from the glass is small, and SiO is added ₂Etc. soda lime glass is also commercially available, and therefore the soda lime glass can be used. In addition, in order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film may be provided on at least one surface of the substrate 101, and particularly, in the case where a synthetic resin plate, film or sheet having low gas barrier property is used as the substrate 101, it is preferable to provide a gas barrier film.

4. Anode of organic electroluminescent element

The anode 102 functions to inject holes into the light-emitting layer 105. Further, when the hole injection layer 103 and/or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. 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 Oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black (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. Further, it can be suitably selected from substances used as an anode of an organic EL element.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light-emitting element, but is preferably low in terms of power consumption of the light-emitting element. For example, an ITO substrate of 300. omega./□ or less functions as an element electrode, but since a substrate of about 10. omega./□ can be provided conventionally, a low-resistance product of, for example, 100. omega./□ to 5. omega./□, preferably 50. omega./□ to 5. omega./□, is particularly preferably used. The thickness of ITO can be arbitrarily selected depending on the resistance value, but it is usually used in a range of 50nm to 300nm in many cases.

5. Hole injection layer and hole transport layer of organic electroluminescent element

The hole injection layer 103 functions to efficiently inject holes transferred from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 functions to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 through 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 kinds of hole injection/transport materials, or are formed by mixing a hole injection/transport material and a polymer binder. In addition, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form a layer.

The hole injecting/transporting substance needs to efficiently inject/transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable that the hole injecting efficiency is high and the injected holes are efficiently transported. Therefore, a substance having a small ionization potential, a large hole mobility, and excellent stability, and in which impurities serving as traps are not easily generated during production and use, is preferable.

As the material for forming the hole injection layer 103 and the hole transport layer 104, any material can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials and conventional materials used for hole injection layers and hole transport layers in p-type semiconductors and organic EL devices. Specific examples of these materials are carbazole derivatives (e.g., N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) and bis (N-alkylcarbazole), triarylamine derivatives (e.g., polymers having an aromatic tertiary amino group in the main chain or side chain, 1-bis (4-di-p-tolylaminophenyl) cyclohexane, N '-diphenyl-N, N' -di (3-methylphenyl) -4,4 '-diaminobiphenyl, N' -diphenyl-N, N '-dinaphthyl-4, 4' -diaminobiphenyl, etc.) Biphenylyl, N '-diphenyl-N, N' -di (3-methylphenyl) -4,4 '-diphenyl-1, 1' -diamine, N '-dinaphthyl-N, N' -diphenyl-4, 4 '-diphenyl-1, 1' -diamine, N⁴,N⁴' -Diphenyl-N⁴,N⁴'-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]4,4' -diamine, N⁴,N⁴,N⁴',N⁴'-tetrakis [1,1' -biphenyl]-4-yl- [1,1' -biphenyl]-4,4' -diamine, 4' -tris (3-methylphenyl (phenyl) amino) triphenylamine, N- ([1,1' -biphenyl]-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, N-bis (4- (dibenzo [ b, d)]Furan-4-yl) phenyl) - [1, 1': 4', 1' -terphenyl]Triphenylamine derivatives such as-4-amine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9, 12-hexaazatriphenylene-2, 3,6,7,10, 11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonate or styrene derivative, polyvinylcarbazole, polysilane, or the like having the monomer in the side chain is preferable, but there is no particular limitation as long as it is a compound which forms a thin film necessary for manufacturing a light-emitting element, and which can inject holes from an anode and can further transport holes.

In addition, it is also known that the conductivity of an organic semiconductor is strongly affected by its doping (doping). Such an organic semiconductor matrix (matrix) substance contains a compound having a good electron donating property or a compound having a good electron accepting property. For the doping of electron-donating substances, strong electron acceptors such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluorotetracyanoquinodimethane (2,3,5, 6-tetrafluorolotetracynano-1, 4-benzoquinodimethane (2,3,5, 6-tetrafluoro-1, 4-benzoquinodimethane, F4TCNQ) are known (see, for example, documents "m. faffy, a. bayer, t. frietz, k. rio (m.pfeiffer, a.beyer, t.fritz, k.leo)," applied physics article (app. phys.lett.), 73- (22), 3202-4 (1998) "and documents" j. bulovertz, m. faffy, t. friez, k. litt. pff.731, p. teff, k.73-k., "applied physics article" (app. k.3, p.p.), "applied physics article"). They generate so-called holes by an electron transfer process in an electron-donating base substance (hole-transporting substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. As a matrix material having a hole transporting property, for example, a benzidine derivative (N, N ' -bis (3-methylphenyl) -N, N ' -bis (phenyl) benzidine (TPD), etc.) or a starburst amine derivative (4,4',4 ″ -tris (N, N-diphenylamino) triphenylamine, TDATA, etc.), or a specific metal phthalocyanine (particularly zinc phthalocyanine (ZnPc), etc.) is known (japanese patent laid-open publication No. 2005-167175).

6. Cathode of organic electroluminescent element

The cathode 108 functions to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.

The material forming the cathode 108 is not particularly limited as long as it is a material capable of efficiently injecting electrons into the organic layer, and the same material as the material 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, and alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride and aluminum) are preferable. In order to improve the electron injection efficiency to improve the element characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. In general, however, these low work function metals are most often unstable in the atmosphere. In order to improve the above-mentioned aspect, for example, a method of doping a minute amount of lithium, cesium, or magnesium into an organic layer and using an electrode having high stability is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. But is not limited thereto.

Further, the following are preferable examples: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals for protecting the electrodes; and inorganic substances such as silicon dioxide, titanium dioxide, and silicon nitride; polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, and the like. The method of manufacturing these electrodes is not particularly limited as long as conduction can be achieved by resistance heating, electron beam evaporation, sputtering, ion plating, coating, or the like.

7. Binder usable in each layer of organic electroluminescent element

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 may be formed as individual layers, or may be dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide (polyphenylene oxide), polybutadiene, a hydrocarbon resin, a ketone resin, a phenoxy resin, polyamide, ethyl cellulose, a vinyl acetate resin, an Acrylonitrile-Butadiene-Styrene (ABS) resin, or a polyurethane resin as a polymer binder, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, or silicone resin.

Method for making organic electroluminescent element

Each layer constituting the organic EL element can be formed by forming a material constituting each layer into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, ink jet, spin coating, casting, or coating. The film thickness of each layer formed in the above-described manner is not particularly limited, and may be appropriately set according to the properties of the material, but is usually in the range of 2nm to 5000 nm. The film thickness can be measured by a crystal oscillation type film thickness measuring apparatus or the like. When a thin film is formed by a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the target crystal structure and the association structure of the film, and the like. The deposition conditions are preferably set in the range of a boat heating temperature of +50 ℃ to +400 ℃, a vacuum degree of 10-6Pa to 10-3Pa, a deposition rate of 0.01 nm/sec to 50 nm/sec, a substrate temperature of-150 ℃ to +300 ℃, and a film thickness of 2nm to 5 μm.

Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element including an anode, a hole injection layer, a hole transport layer, a light-emitting layer including a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described. An anode is formed by forming a thin film of an anode material on an appropriate substrate by vapor deposition or the like, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A target organic EL element is obtained by co-evaporating a host material and a dopant material on the thin film to form a thin film as a light-emitting layer, forming an electron transport layer and an electron injection layer on the light-emitting layer, and further forming a thin film containing a substance for a cathode as a cathode by an evaporation method or the like. In the production of the organic EL element, 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 may be produced in the order of reverse production.

When a dc voltage is applied to the organic EL element obtained as described above, the anode may be applied with a + polarity and the cathode may be applied with a-polarity, and when a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or translucent electrode side (anode or cathode, or both). In addition, the organic EL element emits light even when a pulse current or an alternating current is applied thereto. Further, the waveform of the applied alternating current may be arbitrary.

Application example of organic electroluminescent element

In addition, the present invention is also applicable to a display device including an organic EL element, an illumination device including an organic EL element, or the like.

The display device or the lighting device including the organic EL element can be manufactured by a conventional method such as connecting the organic EL element of this embodiment to a conventional driving device, and can be suitably driven by a conventional driving method such as dc driving, pulse driving, or ac driving.

Examples of the display device include: a panel display (panel display) such as a color flat panel display (color flat display), a flexible display such as a flexible color organic Electroluminescence (EL) display, and the like (see, for example, japanese patent laid-open No. 10-335066, japanese patent laid-open No. 2003-321546, japanese patent laid-open No. 2004-281086, and the like). Examples of the display mode of the display include a matrix (matrix) mode and a segment (segment) mode. In addition, the matrix display and the segment display may coexist in the same panel.

The matrix is a matrix in which pixels for display are two-dimensionally arranged in a lattice shape, a mosaic shape, or the like, and characters or images are displayed by a set of pixels. The shape or size of the pixel is determined according to the application. For example, in image and character display of a personal computer, a monitor, and a television, a rectangular pixel having a side of 300 μm or less is generally used, and in the case of a large-sized display such as a display panel, a pixel having a side of mm level is used. In the case of monochrome display, pixels of the same color may be arranged, and in the case of color display, pixels of red, green, and blue are arranged in parallel to perform display. In this case, a triangular shape and a striped shape are typical. Also, as a driving method of the matrix, any one of a line-sequential (line-sequential) driving method or an active matrix may be used. The line sequential driving has an advantage of a simple structure, but when the operation characteristics are taken into consideration, the active matrix is sometimes more excellent, and therefore the driving method needs to be used separately depending on the application.

In the segmentation method (type), a pattern (pattern) is formed so as to display predetermined information, and the determined region is caused to emit light. Examples thereof include: time and temperature display of a digital clock or a thermometer, operation state display of an audio device or an induction cooker, panel display of an automobile, and the like.

Examples of the illumination device include an illumination device such as an indoor illumination, and a backlight (backlight) of a liquid crystal display device (see, for example, japanese patent laid-open nos. 2003-257621, 2003-277741, and 2004-119211). The backlight is used mainly for the purpose of improving visibility of a display device which does not emit light, and is used for a liquid crystal display device, a timepiece, an audio device, an automobile panel, a display panel, a logo, and the like. In particular, as a backlight for personal computer applications, which has a problem of thinning of a liquid crystal display device, the backlight using the light emitting element of the present embodiment has features of thinness and lightweight, considering that thinning is difficult due to inclusion of a fluorescent lamp or a light guide plate in the conventional system.

[ examples ]

The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples. First, a synthesis example of the compounds used in the examples will be described below.

Synthesis example (1-1): synthesis of Compound (1-1)

[ chemical 239]

Compound (1-1) was synthesized according to the method described in International publication No. 2006/003842.

Synthesis example (1-2): synthesis of Compound (1-12)

[ solution 240]

The compounds (1 to 12) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 3): synthesis of Compound (1-16)

[ solution 241]

The compounds (1 to 16) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 4): synthesis of Compound (1-47)

[ solution 242]

The compounds (1 to 47) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 5): synthesis of Compound (1-153)

[ solution 243]

The compounds (1-153) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 6): synthesis of Compound (1-255)

[ chemical 244]

The compounds (1 to 255) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 7): synthesis of Compound (1-263)

[ chemical 245]

The compounds (1-263) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 8): synthesis of Compound (1-319)

[ solution 246]

The compounds (1 to 319) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 9): synthesis of Compound (1-454)

[ formulation 247]

The compound (1-454) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 496.

[ chemical 248]

Synthesis examples (1 to 10): synthesis of Compound (1-457)

[ Hua 249]

The compound (1-457) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 596.

[ solution 250]

Synthesis examples (1 to 11): synthesis of Compound (1-456)

[ solution 251]

The compound (1-456) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 596.

[ solution 252]

Synthesis examples (1 to 12): synthesis of Compound (1-490)

[ solution 253]

The compound (1-490) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 546.

[ solution 254]

Synthesis examples (1 to 13): synthesis of Compound (1-493)

[ solution 255]

The compound (1-493) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 646.

[ solution 256]

Synthesis examples (1 to 14): synthesis of Compound (1-492)

[ solution 257]

The compound (1-492) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 646.

[ Hua 258]

Synthesis examples (1 to 15): synthesis of Compound (1-641)

[ solution 259]

The compounds (1-641) were synthesized according to the method described in International publication No. 2009/142230.

Synthesis examples (1 to 16): synthesis of Compound (1-646)

[ solution 260]

The compounds (1-646) were synthesized according to the method described in International publication No. 2009/142230.

Synthesis examples (1 to 17): synthesis of Compound (1-649)

[ solution 261]

The compounds (1-649) were synthesized according to the method described in International publication No. 2009/142230.

Synthesis examples (1 to 18): synthesis of Compound (1-640)

[ solution 262]

The compounds (1-640) were synthesized according to the method described in International publication No. 2009/142230.

Synthesis examples (1 to 19): synthesis of Compound (1-535)

[ solution 263]

The compounds (1-535) were synthesized according to the method described in International publication No. 2009/142230.

Synthesis examples (1 to 20): synthesis of Compound (1-534)

[ chemical 264]

The compounds (1-534) were synthesized according to the method described in International publication No. 2009/142230.

Synthesis examples (1 to 21): synthesis of Compound (1-677)

[ solution 265]

The compounds (1-677) were synthesized by appropriately changing the starting compounds according to the method described in International publication No. 2009/142230. EI-MS: and m/z is 708.

Synthesis examples (1 to 22): synthesis of Compound (1-682)

[ solution 266]

Compound (1-682) was synthesized by appropriately changing the method described in International publication No. 2009/142230. EI-MS: 784 as m/z.

Synthesis examples (1 to 23): synthesis of Compound (1-1334)

[ solution 267]

The compound (1-1334) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 587.

[ solution 268]

Synthesis examples (1 to 24): synthesis of Compound (1-1336)

[ 269]

The compound (1-1336) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 637.

[ solution 270]

Synthesis examples (1 to 25): synthesis of Compound (1-279)

[ 271]

The compound (1-279) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 737/z.

[ solution 272]

Synthesis examples (1 to 26): synthesis of Compound (1-125)

[ 273]

The compounds (1 to 125) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 27): synthesis of Compound (1-155)

[ solution 274]

The compounds (1-155) were synthesized according to the method described in International publication No. 2006/003842.

Synthesis examples (1 to 28): synthesis of Compound (1-29)

[ design 275]

The compound (1-29) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 587.

[ 276]

Synthesis examples (1 to 29): synthesis of Compound (1-276)

[ Hua 277]

The compound (1-276) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 637.

[ 278]

Synthesis examples (1 to 30): synthesis of Compound (1-448)

[ chemical No. 279]

The compound (1-448) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 671.

[ solution 280]

Synthesis examples (1 to 31): synthesis of Compound (1-13)

[ Hua 281]

The compounds (1-13) were synthesized by appropriately changing the starting compounds according to the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 658.

[ solution 282]

Synthesis examples (1 to 32): synthesis of Compound (1-287)

[ 283] chemical reaction

The compounds (1-287) were synthesized by appropriately modifying the starting compounds according to the methods described in Korean laid-open patent publication Nos. 2017 and 116885. EI-MS: and m/z is 532.

[ CHEMICAL 284]

Synthesis examples (1 to 33): synthesis of Compound (1-124)

[ solution 285]

The compound (1-124) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 482.

[ solution 286]

Synthesis examples (1 to 34): synthesis of Compound (1-4)

[ CHEMICAL 287]

The compound (1-4) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 558.

[ solution 288]

Synthesis examples (1 to 35): synthesis of Compound (1-807)

[ 289]

The compound (1-807) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 546.

[ solution 290]

Synthesis examples (1 to 36): synthesis of Compound (1-802)

[ formulation 291]

The compound (1-802) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 496.

[ solution 292]

Synthesis examples (1 to 37): synthesis of Compound (1-2400)

[ Hua 293]

The compound (1-2400) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 532.

[ solution 294]

Synthesis examples (1 to 38): synthesis of Compound (1-2401)

[ solution 295]

The compound (1-2401) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 482.

[ solution 296]

Synthesis examples (1 to 39): synthesis of Compound (1-4133)

The compound (1-4133) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 609.

[ Hua 297]

Synthesis examples (1 to 40): synthesis of Compound (1-148)

The compound (1-148) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 533.

[ 298]

Synthesis examples (1 to 41): synthesis of Compound (1-150)

The compound (1-150) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 633.

[ 299]

Synthesis examples (1 to 42): synthesis of Compound (1-136)

The compound (1-136) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 533.

[ equation 300]

Synthesis examples (1 to 43): synthesis of Compound (1-4155)

The compound (1-4155) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 583.

[ solution 301]

Synthesis examples (1 to 44): synthesis of Compound (1-3268)

The compound (1-3268) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 302]

Synthesis examples (1 to 45): synthesis of Compound (1-4114)

The compound (1-4114) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 303]

Synthesis examples (1 to 46): synthesis of Compound (1-4121)

The compound (1-4121) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 304]

Synthesis examples (1 to 47): synthesis of Compound (1-4119)

The compound (1-4119) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 305]

Synthesis examples (1 to 48): synthesis of Compound (1-4120)

The compound (1-4120) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 663 is given as m/z.

[ solution 306]

Synthesis examples (1 to 49): synthesis of Compound (1-4107)

The compound (1-4107) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 663 is given as m/z.

[ solution 307]

Synthesis examples (1 to 50): synthesis of Compound (1-4317)

The compound (1-4317) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 583.

[ chemical 308]

Synthesis examples (1 to 51): synthesis of Compound (1-4327)

The compound (1-4327) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 633.

[ solution 309]

Synthesis examples (1 to 52): synthesis of Compound (1-3991)

The compound (1-3991) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ chemical 310]

Synthesis examples (1 to 53): synthesis of Compound (1-2984)

The compound (1-2984) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 311]

Synthesis examples (1 to 54): synthesis of Compound (1-3452)

The compound (1-3452) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 649.

[ solution 312]

Synthesis examples (1 to 55): synthesis of Compound (1-2883)

The compound (1-2883) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 649.

[ solution 313]

Synthesis examples (1 to 56): synthesis of Compound (1-4205)

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

[ chemical 314]

Synthesis examples (1 to 57): synthesis of Compound (1-4232)

Compound (1-4232) was synthesized by appropriately changing the starting compound in the method described in synthetic examples (1-56). EI-MS: m/z 658.

[ solution 315]

Synthesis examples (1 to 58): synthesis of Compound (1-4219)

Compound (1-4219) was synthesized by appropriately changing the starting compound in the method described in synthetic examples (1-56). EI-MS: m/z 608.

[ chemical 316]

Synthesis examples (1 to 59): synthesis of Compound (1-4254)

Compound (1-4254) was synthesized by appropriately changing the starting compound in the method described in synthetic examples (1-56). EI-MS: and m/z is 634.

[ chemical 317]

Synthesis examples (1 to 60): synthesis of Compound (1-4263)

Compound (1-4263) was synthesized by appropriately changing the starting compound in the method described in synthetic examples (1-56). EI-MS: m/z 658.

[ solution 318]

Synthesis examples (1 to 61): synthesis of Compound (1-4271)

Compound (1-4271) was synthesized by appropriately changing the starting compound in the method described in synthetic examples (1-56). EI-MS: and m/z is 708.

[ formulation 319]

Synthesis examples (1 to 62): synthesis of Compound (1-2995)

The compound (1-2995) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: and m/z is 648.

[ solution 320]

Synthesis examples (1 to 63): synthesis of Compound (1-3005)

The compounds (1 to 3005) were synthesized by appropriately changing the starting compounds in the methods described in the synthesis examples (1 to 56). EI-MS: and m/z is 648.

[ solution 321]

Synthesis examples (1 to 64): synthesis of Compound (1-3020)

The compound (1-3020) was synthesized by appropriately changing the starting compound in the method described in the above synthesis example (1-56). EI-MS: and m/z is 750.

[ solution 322]

Synthesis examples (1 to 65): synthesis of Compound (1-4204)

The compound (1-4204) was synthesized by appropriately changing the starting compound according to the method described in the above synthesis example (1-56). EI-MS: and m/z is 708.

[ solution 323]

Synthesis examples (1 to 66): synthesis of Compound (1-4198)

The compound (1-4198) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: 788 m/z.

[ solution 324]

Synthesis examples (1 to 67): synthesis of Compound (1-4280)

Compound (1-4280) was synthesized by appropriately changing the starting compound in the method described in synthetic examples (1-56). EI-MS: m/z 734.

[ solution 325]

Synthesis examples (1 to 68): synthesis of Compound (1-3821)

Compound (1-3821) was synthesized by appropriately changing the starting compound in the method described in the above synthetic examples (1-56). EI-MS: m/z 838.

[ chemical 326]

Synthesis examples (1 to 69): synthesis of Compound (1-3078)

The compound (1-3078) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: and m/z is 648.

[ solution 327]

Synthesis examples (1 to 70): synthesis of Compound (1-4209)

The compound (1-4209) was synthesized by appropriately changing the starting compound according to the method described in the above synthesis example (1-56). EI-MS: m/z 658.

[ solution 328]

Synthesis examples (1 to 71): synthesis of Compound (1-4093)

The compound (1-4093) was synthesized by appropriately changing the starting compound according to the method described in korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 609.

[ solution 329]

Synthesis examples (1 to 72): synthesis of Compound (1-4092)

The compound (1-4092) was synthesized by appropriately changing the starting compound according to the method described in korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 811.

[ solution 330]

Synthesis examples (1 to 73): synthesis of Compound (1-2977)

The compound (1-2977) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 699 for m/z.

[ solution 331]

Synthesis examples (1 to 74): synthesis of Compound (1-4036)

The compound (1-4036) was synthesized by appropriately modifying the starting compound according to the method described in korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 649.

[ chemical 332]

Synthesis examples (1 to 75): synthesis of Compound (1-4335)

The compound (1-4335) was synthesized by appropriately changing the starting compound in the method described in the above synthesis example (1-56). EI-MS: and m/z 609.

[ 333]

Synthesis examples (1 to 76): synthesis of Compound (1-4347)

The compound (1-4347) was synthesized by appropriately changing the starting compound in the method described in the above synthesis example (1-56). EI-MS: and m/z 609.

[ chemical formula 334]

Synthesis examples (1 to 77): synthesis of Compound (1-4354)

The compound (1-4354) was synthesized by appropriately changing the starting compound in the method described in the above synthesis example (1-56). EI-MS: and m/z 659.

[ solution 335]

Synthesis examples (1 to 78): synthesis of Compound (1-3751)

The compounds (1 to 3751) were synthesized by appropriately changing the starting compounds in the methods described in the above synthesis examples (1 to 56). EI-MS: and m/z is 649.

[ 336]

Synthesis examples (1 to 79): synthesis of Compound (1-4106)

The compound (1-4106) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 609.

[ solution 337]

Synthesis examples (1 to 80): synthesis of Compound (1-3830)

The compound (1-3830) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 533.

[ solution 338]

Synthesis examples (1 to 81): synthesis of Compound (1-3839)

The compound (1-3839) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 533.

[ chemical 339]

Synthesis examples (1 to 82): synthesis of Compound (1-4381)

The compound (1-4381) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 583.

[ solution 340]

Synthesis examples (1 to 83): synthesis of Compound (1-4390)

The compound (1-4390) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 633.

[ solution 341]

Synthesis examples (1 to 84): synthesis of Compound (1-3837)

The compound (1-3837) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 713.

[ solution 342]

Synthesis examples (1 to 85): synthesis of Compound (1-4091)

The compound (1-4091) was synthesized by appropriately changing the starting compound according to the method described in korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 533.

[ solution 343]

Synthesis examples (1 to 86): synthesis of Compound (1-3859)

The compound (1-3859) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 583.

[ solution 344]

Synthesis examples (1 to 87): synthesis of Compound (1-2416)

The compound (1-2416) was synthesized by appropriately changing the starting compound according to the method described in korean laid-open patent publication No. 2019-056338. EI-MS: m/z is 583.

[ solution 345]

Synthesis examples (1 to 88): synthesis of Compound (1-2495)

The compound (1-2495) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2019-056338. EI-MS: and m/z is 749.

[ 346]

Synthesis examples (1 to 89): synthesis of Compound (1-2404)

The compound (1-2404) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2019-056338. EI-MS: and m/z is 673.

[ 347]

Synthesis examples (1 to 90): synthesis of Compound (1-2440)

The compound (1-2440) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2019-056338. EI-MS: and m/z is 965.

[ Hua 348]

Synthesis examples (1 to 91): synthesis of Compound (1-2499)

The compound (1-2499) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2019-056338. EI-MS: and m/z is 749.

[ chemical 349]

Synthesis examples (1 to 92): synthesis of Compound (1-2413)

The compound (1-2413) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2019-056338. EI-MS: 723 m/z.

[ solution 350]

Synthesis examples (1 to 93): synthesis of Compound (1-2520)

The compound (1-2520) was synthesized by the method described in Korean laid-open patent publication No. 2010-007791. EI-MS: and m/z 659.

[ solution 351]

Synthesis examples (1 to 94): synthesis of Compound (1-2516)

The compound (1-2516) was synthesized by appropriately changing the method described in korean laid-open patent publication No. 2010-007791. EI-MS: 839 is m/z.

[ solution 352]

Synthesis examples (1 to 95): synthesis of Compound (1-2519)

The compound (1-2519) was synthesized by appropriately changing the method described in korean laid-open patent publication No. 2010-007791. EI-MS: and m/z is 749.

[ Change 353]

Synthesis examples (1 to 96): synthesis of Compound (1-2525)

The compound (1-2525) was synthesized by appropriately changing the method described in korean laid-open patent publication No. 2010-007791. EI-MS: and m/z is 749.

[ solution 354]

Synthesis examples (1 to 97): synthesis of Compound (1-2541)

The compound (1-2541) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 659.

[ solution 355]

Synthesis examples (1 to 98): synthesis of Compound (1-2557)

The compound (1-2557) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 659.

[ chemical 356]

Synthesis examples (1 to 99): synthesis of Compound (1-2573)

The compound (1-2573) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 709.

[ chemical 357]

Synthesis examples (1 to 100): synthesis of Compound (1-2586)

The compound (1-2586) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 709.

[ 358]

Synthesis examples (1 to 101): synthesis of Compound (1-2594)

The compound (1-2594) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 709.

[ 359]

Synthesis examples (1 to 102): synthesis of Compound (1-2599)

The compound (1-2599) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 709.

[ solution 360]

Synthesis examples (1 to 103): synthesis of Compound (1-2728)

The compound (1-2728) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 749.

[ solution 361]

Synthesis examples (1 to 104): synthesis of Compound (1-2579)

The compound (1-2579) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 889 m/z.

[ solution 362]

Synthesis examples (1 to 105): synthesis of Compound (1-2696)

The compound (1-2696) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 889 m/z.

[ solution 363]

Synthesis examples (1 to 106): synthesis of Compound (1-2738)

The compound (1-2738) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 799.

[ solution 364]

Synthesis examples (1 to 107): synthesis of Compound (1-2743)

The compound (1-2743) was synthesized by appropriately changing the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 799.

[ solution 365]

Synthesis examples (1 to 108): synthesis of Compound (1-2699)

The compound (1-2699) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 1041.

[ solution 366]

Synthesis examples (1 to 109): synthesis of Compound (1-2603)

The compound (1-2603) was synthesized by the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 749.

[ 367]

Synthesis examples (1 to 110): synthesis of Compound (1-2756)

The compound (1-2756) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 925.

[ solution 368]

Synthesis examples (1-111): synthesis of Compound (1-2627)

The compound (1-2627) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 749.

[ Hua 369]

Synthesis examples (1 to 112): synthesis of Compound (1-2757)

The compound (1-2757) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 799.

[ solution 370]

Synthesis examples (1 to 113): synthesis of Compound (1-2686)

The compound (1-2686) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 749.

[ 371]

Synthesis examples (1 to 114): synthesis of Compound (1-2615)

The compound (1-2615) was synthesized by appropriately changing the starting compound according to the method described in korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 749.

[ CHEMICAL 372]

Synthesis examples (1 to 115): synthesis of Compound (1-2640)

The compound (1-2640) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 749.

[ 373]

Synthesis examples (1 to 116): synthesis of Compound (1-2747)

The compound (1-2747) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: 839 is m/z.

[ solution 374]

Synthesis examples (1 to 117): synthesis of Compound (1-2641)

The compound (1-2641) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2018-0131963. EI-MS: and m/z is 929.

[ solution 375]

Synthesis examples (1 to 118): synthesis of Compound (1-2775)

The compound (1-2775) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 735 m/z.

[ chemical 376]

Synthesis examples (1 to 119): synthesis of Compound (1-2779)

The compound (1-2779) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 735 m/z.

[ 377]

Synthesis examples (1 to 120): synthesis of Compound (1-2787)

The compound (1-2787) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 785 m/z.

[ chemical 378]

Synthesis examples (1 to 121): synthesis of Compound (1-2776)

The compound (1-2776) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 915.

[ solution 379]

Synthesis examples (1 to 122): synthesis of Compound (1-2812)

The compound (1-2812) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 825.

[ 380]

Synthesis examples (1 to 123): synthesis of Compound (1-3914)

The compound (1-3914) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 659.

[ chemical 381]

Synthesis examples (1 to 124): synthesis of Compound (1-3951)

The compound (1-3951) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 749.

[ Hua 382]

Synthesis examples (1 to 125): synthesis of Compound (1-3903)

The compound (1-3903) was synthesized by appropriately changing the starting compound according to the method described in korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 659.

[ 383]

Synthesis examples (1 to 126): synthesis of Compound (1-1335)

The compound (1-1335) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 587.

[ 384]

Synthesis examples (1 to 127): synthesis of Compound (1-1337)

The compound (1-1337) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 637.

[ solution 385]

Synthesis examples (1 to 128): synthesis of Compound (1-28)

The compounds (1-28) were synthesized according to the methods described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 587.

[ solution 386]

Synthesis examples (1 to 129): synthesis of Compound (1-275)

The compound (1-275) was synthesized according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 637.

[ 387]

Synthesis examples (1 to 130): synthesis of Compound (1-3445)

The compound (1-3445) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ 388]

Synthesis examples (1 to 131): synthesis of Compound (1-3467)

The compound (1-3467) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ Hua 389]

Synthesis examples (1 to 132): synthesis of Compound (1-3434)

The compound (1-3434) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 390]

Synthesis examples (1 to 133): synthesis of Compound (1-3481)

The compound (1-3481) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ 391]

Synthesis examples (1 to 134): synthesis of Compound (1-3408)

The compound (1-3408) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ 392]

Synthesis examples (1 to 135): synthesis of Compound (1-3777)

The compound (1-3777) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 589.

[ 393]

Synthesis examples (1 to 136): synthesis of Compound (1-3594)

The compound (1-3594) was synthesized by appropriately modifying the starting compound according to the method described in korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ 394]

Synthesis examples (1 to 137): synthesis of Compound (1-3589)

The compound (1-3589) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ Hua 395]

Synthesis examples (1 to 138): synthesis of Compound (1-3440)

The compound (1-3440) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 673.

[ 396]

Synthesis examples (1 to 139): synthesis of Compound (1-3435)

The compound (1-3435) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 753.

[ solution 397]

Synthesis examples (1 to 140): synthesis of Compound (1-3572)

The compound (1-3572) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 699 for m/z.

[ solution 398]

Synthesis examples (1-141): synthesis of Compound (1-3453)

The compound (1-3453) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 825.

[ 399]

Synthesis examples (1-142): synthesis of Compound (1-3562)

The compound (1-3562) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ solution 400]

Synthesis examples (1-143): synthesis of Compound (1-3559)

The compound (1-3559) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ solution 401]

Synthesis examples (1 to 144): synthesis of Compound (1-3522)

The compound (1-3522) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 402]

Synthesis examples (1-145): synthesis of Compound (1-4014)

The compound (1-4014) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 739.

[ chemical formula 403]

Synthesis examples (1 to 146): synthesis of Compound (1-4018)

The compound (1-4018) was synthesized by appropriately modifying the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ chemical formula 404]

Synthesis examples (1 to 147): synthesis of Compound (1-3762)

The compound (1-3762) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ solution 405]

Synthesis examples (1 to 148): synthesis of Compound (1-2912)

The compound (1-2912) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ chemical 406]

Synthesis examples (1 to 149): synthesis of Compound (1-3284)

The compound (1-3284) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 407]

Synthesis examples (1 to 150): synthesis of Compound (1-3736)

The compound (1-3736) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 649.

[ solution 408]

Synthesis examples (1-151): synthesis of Compound (1-3770)

The compound (1-3770) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 589.

[ 409]

Synthesis examples (1 to 152): synthesis of Compound (1-2873)

The compound (1-2873) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 648.

[ solution 410]

Synthesis examples (1-153): synthesis of Compound (1-3249)

The compound (1-3249) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ solution 411]

Synthesis examples (1 to 154): synthesis of Compound (1-3296)

The compound (1-3296) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ chemical 412]

Synthesis example (1-155): synthesis of Compound (1-2917)

The compound (1-2917) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 803.

[ solution 413]

Synthesis examples (1 to 156): synthesis of Compound (1-3768)

The compound (1-3768) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 723 m/z.

[ solution 414]

Synthesis examples (1 to 157): synthesis of Compound (1-3780)

The compound (1-3780) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 789 m/z.

[ solution 415]

Synthesis examples (1 to 158): synthesis of Compound (1-3963)

The compound (1-3963) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ chemical 416]

Synthesis examples (1 to 159): synthesis of Compound (1-4112)

The compound (1-4112) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 649.

[ chemical formula 417]

Synthesis examples (1 to 160): synthesis of Compound (1-4052)

The compound (1-4052) was synthesized by appropriately changing the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 699 for m/z.

[ solution 418]

Synthesis examples (1 to 161): synthesis of Compound (1-4047)

The compound (1-4047) was synthesized by appropriately changing the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 649.

[ solution 419]

Synthesis examples (1 to 162): synthesis of Compound (1-3778)

The compound (1-3778) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 748.

[ solution 420]

Synthesis examples (1-163): synthesis of Compound (1-4008)

The compound (1-4008) was synthesized by appropriately changing the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 497.

[ 421]

Synthesis examples (1 to 164): synthesis of Compound (1-802)

The compound (1-802) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 497.

[ solution 422]

Synthesis examples (1 to 165): synthesis of Compound (1-804)

The compound (1-804) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 513.

[ solution 423]

Synthesis examples (1 to 166): synthesis of Compound (1-3784)

The compound (1-3784) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 547.

[ chemical 424]

Synthesis examples (1-167): synthesis of Compound (1-808)

The compound (1-808) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 547.

[ formation 425]

Synthesis examples (1-168): synthesis of Compound (1-801)

The compound (1-801) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 572.

[ chemical 426]

Synthesis examples (1 to 169): synthesis of Compound (1-4142)

The compound (1-4142) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 713.

[ solution 427]

Synthesis examples (1 to 170): synthesis of Compound (1-4145)

The compound (1-4145) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z 865.

[ solution 428]

Synthesis examples (1-171): synthesis of Compound (1-4138)

The compound (1-4138) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 713.

[ 429]

Synthesis examples (1 to 172): synthesis of Compound (1-4165)

The compound (1-4165) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 713.

[ solution 430]

Synthesis examples (1 to 173): synthesis of Compound (1-4168)

The compound (1-4168) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 713.

[ Hua 431]

Synthesis examples (1 to 174): synthesis of Compound (1-4152)

The compound (1-4152) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 713.

[ formulation 432]

Synthesis examples (1 to 175): synthesis of Compound (1-4143)

The compound (1-4143) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 623 m/z.

[ solution 433]

Synthesis examples (1 to 176): synthesis of Compound (1-3849)

The compound (1-3849) was synthesized by appropriately changing the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 863.

[ chemical 434]

Synthesis examples (1 to 177): synthesis of Compound (1-4434)

The compound (1-4434) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 601/z.

[ Hua 435]

Synthesis examples (1 to 178): synthesis of Compound (1-4429)

The compound (1-4429) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 601/z.

[ solution 436]

Synthesis examples (1 to 179): synthesis of Compound (1-4458)

The compound (1-4458) was synthesized by appropriately changing the starting compound in the method described in the above synthesis example (1-56). EI-MS: 665 m/z.

[ 437]

Synthesis examples (1 to 180): synthesis of Compound (1-4409)

The compound (1-4409) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 587.

[ solution 438]

Synthesis examples (1 to 181): synthesis of Compound (1-4404)

The compound (1-4404) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: m/z is 587.

[ 439]

Synthesis examples (1 to 182): synthesis of Compound (1-4427)

The compound (1-4427) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 615.

[ solution 440]

Synthesis examples (1-183): synthesis of Compound (1-2973)

The compound (1-2973) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z 497.

[ solution 441]

Synthesis examples (1 to 184): synthesis of Compound (1-4747)

The compound (1-4747) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 573.

[ solution 442]

Synthesis examples (1 to 185): synthesis of Compound (1-3444)

The compound (1-3444) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: and m/z is 673.

[ chemical 443]

Synthesis examples (1 to 186): synthesis of Compound (1-3450)

The compound (1-3450) was synthesized by appropriately changing the starting compound according to the method described in Korean laid-open patent publication No. 2017-116885. EI-MS: 725 m/z.

[ solution 444]

Synthesis example (1-187): synthesis of Compound (1-1355)

Compound (1-12) (1g), 5% platinum-carbon (5% Pt/C, 300mg), heavy water (40mL), cyclohexane (cHex, 20mL), and isopropanol (IPA, 5mL) were placed in a flask under an argon atmosphere and heated at 100 ℃. After the reaction, water and chloroform were added to conduct liquid separation extraction, and after the organic layer was dried over magnesium sulfate and filtered, the organic layer was concentrated and the obtained crude product was recrystallized, whereby the objective compound (1-1355) was obtained.

EI-MS：m/z＝532。

[ solution 445]

Synthesis examples (1 to 188): synthesis of Compound (1-1359)

The compound represented by formula (1-1359) was synthesized in the same manner as in the synthesis example (1-187). EI-MS: and m/z is 532.

[ chemical formula 446]

Synthesis examples (1-189): synthesis of Compound (1-1390)

The compound represented by the formula (1-1390) was synthesized by the same method as in the synthesis example (1-187). EI-MS: 668 m/z.

[ 447]

Synthesis examples (1 to 190): synthesis of Compound (1-1496)

The compounds represented by the formula (1-1496) were synthesized by the same method as in the synthesis example (1-187). EI-MS: and m/z is 749.

[ 448]

Synthesis examples (1-191): synthesis of Compound (1-1598)

The compound represented by the formula (1-1598) was synthesized in the same manner as in the above synthesis example (1-187). EI-MS: 584 is equal to m/z.

[ solution 449]

Synthesis examples (1 to 192): synthesis of Compound (1-1658)

The compound represented by formula (1-1658) was synthesized in the same manner as in the above synthesis example (1-187). EI-MS: 584 is equal to m/z.

[ solution 450]

Synthesis example (1-193): synthesis of Compound (1-1789)

The compound represented by formula (1-1789) was synthesized in the same manner as in the above synthesis example (1-187). EI-MS: and m/z is 520.

[ solution 451]

Synthesis example (1-194): synthesis of Compound (1-1791)

The compound represented by formula (1-1791) was synthesized in the same manner as in synthesis example (1-187). EI-MS: and m/z is 624.

[ solution 452]

Synthesis example (1-195): synthesis of Compound (1-1825)

The compound represented by formula (1-1825) was synthesized in the same manner as in synthesis example (1-187). EI-MS: and m/z is 572.

[ solution 453]

Synthesis examples (1 to 196): synthesis of Compound (1-1468)

The compound represented by formula (1-1468) was synthesized by the same method as in synthesis example (1-187). EI-MS: 668 m/z.

[ 454]

Synthesis examples (1-197): synthesis of Compound (1-1498)

The compound represented by formula (1-1498) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z is 908.

[ 455]

Synthesis examples (1 to 198): synthesis of Compound (1-2389)

The compound represented by formula (1-2389) was synthesized in the same manner as in synthesis example (1-187). EI-MS: and m/z is 664.

[ formulation 456]

Synthesis examples (1-199): synthesis of Compound (1-1618)

The compounds represented by the formulae (1-1618) were synthesized by the same method as in the synthesis example (1-187). EI-MS: and m/z is 768.

[ chemical 457]

Synthesis examples (1 to 200): synthesis of Compound (1-1372)

The compound represented by the formula (1-1372) was synthesized by the same method as in the synthesis example (1-187). EI-MS: and m/z 612.

[ 458]

Synthesis example (1-201): synthesis of Compound (1-1615)

The compound represented by the formula (1-1615) was synthesized by the same method as in the synthesis example (1-187). EI-MS: and m/z is 664.

[ Hua 459]

Synthesis example (1-202): synthesis of Compound (1-1783)

The compound represented by formula (1-1783) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z is 704.

[ chemical 460]

Synthesis examples (1 to 203): synthesis of Compound (1-1356)

The compound represented by formula (1-1356) was synthesized in the same manner as in the synthesis example (1-187). EI-MS: 692 as m/z.

[ chemical 461]

Synthesis examples (1 to 204): synthesis of Compound (1-1626)

The compound represented by formula (1-1626) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z 560.

[ solution 462]

Synthesis examples (1 to 205): synthesis of Compound (1-1467)

The compound represented by formula (1-1467) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z is 508.

[ 463]

Synthesis example (1-206): synthesis of Compound (1-1347)

The compounds represented by the formulae (1-1347) were synthesized by the same method as in the synthesis examples (1-187). EI-MS: and m/z 588.

[ formation 464]

Synthesis examples (1 to 207): synthesis of Compound (1-1860)

The compound represented by formula (1-1860) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z is 572.

[ formula 465]

Synthesis examples (1 to 208): synthesis of Compound (1-1855)

The compound represented by formula (1-1855) was synthesized by the same method as in the above synthesis example (1-187). EI-MS: and m/z is 520.

[ 466]

Synthesis examples (1-209): synthesis of Compound (1-2397)

The compound represented by formula (1-2397) was synthesized in the same manner as in synthesis example (1-187). EI-MS: and m/z 560.

[ Hua 467]

Synthesis examples (1 to 210): synthesis of Compound (1-2398)

The compound represented by formula (1-2398) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z is 508.

[ 468]

Synthesis examples (1 to 211): synthesis of Compound (1-4655)

Compound (1-4655) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: and m/z is 526.

[ 469]

Synthesis examples (1 to 212): synthesis of Compound (1-4660)

Compound (1-4660) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: m/z 592.

[ solution 470]

Synthesis examples (1 to 213): synthesis of Compound (1-2388)

The compound represented by formula (1-2388) was synthesized in the same manner as in synthesis example (1-187). EI-MS: and m/z is 613.

[ 471]

Synthesis examples (1 to 214): synthesis of Compound (1-4573)

The compound represented by the formula (1-4573) was synthesized by the same method as in the above synthesis example (1-187). EI-MS: 601/z.

[ solution 472]

Synthesis examples (1 to 215): synthesis of Compound (1-4579)

The compound (1-4579) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: and m/z 588.

[ 473]

Synthesis examples (1 to 216): synthesis of Compound (1-4510)

The compound represented by formula (1-4510) was synthesized in the same manner as in synthesis example (1-187). EI-MS: 601/z.

[ 474]

Synthesis example (1-217): synthesis of Compound (1-4701)

The compound represented by formula (1-4701) was synthesized by the same method as in synthesis example (1-187). EI-MS: and m/z is 640.

[ solution 475]

Synthesis examples (1 to 218): synthesis of Compound (1-4688)

Compound (1-4688) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: and m/z is 631.

[ 476]

Synthesis examples (1 to 219): synthesis of Compound (1-4715)

The compound (1-4715) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: and m/z is 624.

[ 477]

Synthesis examples (1 to 220): synthesis of Compound (1-4565)

The compound represented by formula (1-4565) was synthesized in the same manner as in synthesis example (1-187). EI-MS: and m/z is 680.

[ Hua 478]

Synthesis examples (1 to 221): synthesis of Compound (1-4736)

The compound (1-4736) was synthesized by appropriately changing the starting compound in the method described in the above synthesis examples (1-56). EI-MS: m/z 498.

[ Hua 479]

Synthesis example (2-1): synthesis of Compound (2-41)

[ solution 480]

The compounds (2 to 41) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by (Nuclear Magnetic Resonance, NMR) measurement.

¹H-NMR(500MHz,CDCl₃)：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)

[ Hua 481]

The compounds (2 to 31) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(500MHz,CDCl₃)：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)

[ 482]

The compounds (2 to 46) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 4): synthesis of Compound (2-37)

[ 483]

The compounds (2 to 37) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 5): synthesis of Compound (2-42)

[ solution 484]

The compound represented by the formula (2-42) was synthesized by the same method as in synthesis example (2-1).

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 6): synthesis of Compound (2-49)

[ 485]

The compound (2-49) was synthesized according to the method described in "comparative synthesis example (1)" of Japanese patent laid-open No. 2016-88927.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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),7.43～7.46(m,6H),8.95(d,2H).

Synthesis examples (2 to 7): synthesis of Compound (2-50)

[ 486]

The compounds (2 to 50) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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),7.4～7.5(m,6H),8.9(d,2H).

Synthesis examples (2 to 8): synthesis of Compound (2-53)

[ CHEMICAL 487]

The compounds (2 to 53) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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),7.32～7.35(m,6H),7.56(dd,2H),7.63(d,4H),7.99(d,2H),9.05(d,2H).

Synthesis examples (2 to 9): synthesis of Compound (2-33)

[ 488]

The compounds (2 to 33) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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),7.58～7.64(m,2H),7.67(d,2H),8.86(d,1H),8.96(d,1H).

Synthesis examples (2 to 10): synthesis of Compound (2-508)

[ chemical 489]

4- (tert-amyl) aniline (15.0g) was dissolved in acetonitrile (150ml) under a nitrogen atmosphere, and bromine (22.5g) was added dropwise thereto under cooling in an ice bath and stirred for 0.5 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene), whereby intermediate (I-A) (20.0g) was obtained.

[ solution 490]

Copper chloride (10.1g) and intermediate (I-A) (20.0g) were dissolved in acetonitrile (100ml) under a nitrogen atmosphere, and tert-butyl nitrite (9.6g) dissolved in acetonitrile (50ml) was added dropwise thereto at 60 ℃ and stirred at the same temperature for 0.5 hour. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene/heptane 1/4 (volume ratio)), whereby intermediate (I-B) (19.0g) was obtained.

[ 491]

Intermediate (I-B) (10.0g), bis (4-tert-butylphenyl) amine (18.2g), dichlorobis (di-tert-butyl (4-dimethylaminophenyl) phosphino) palladium (Pd-132, 0.21g) as a palladium catalyst, sodium tert-butoxide (NaOtBu, 7.1g) and xylene (100ml) were placed in a flask and heated at 100 ℃ for 1 hour under a nitrogen atmosphere. After the reaction, water and toluene were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene), whereby intermediate (I-C) (18.0g) was obtained.

[ 492]

To a flask containing intermediate (I-C) (18.0g) and tert-butylbenzene (500ml) was added 1.56M t-butyllithium pentane solution (28.9ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 0.5 hour, and then the component having a boiling point lower than that of t-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (11.3g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled to 0 ℃ again, N-diisopropylethylamine (5.8g) was added thereto, and after stirring at room temperature until heat generation ended, it was heated to 100 ℃ and stirred with heating for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath was added thereto, followed by ethyl acetate. After the organic layer was concentrated, it was purified by a short column of silica gel (eluent: toluene). The obtained crude product was recrystallized using chlorobenzene, whereby compound (2-508) (7.1g) was obtained.

[ 493]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 11): synthesis of Compound (2-538)

[ 494]

Under nitrogen atmosphere, 3,4, 5-trichloroaniline (12.0g), d⁵Bromobenzene (30.0g), dichlorobis (di-tert-butyl (4-dimethylaminophenyl) phosphino) palladium (Pd-132, 0.43g) as a palladium catalyst, sodium tert-butoxide (NaOtBu, 14.7g) and xylene (200mL) were placed in a flask and heated at 120 ℃ for 3 hours. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene/heptane 1/1 (volume ratio)), whereby 15.0g of intermediate (I-D) was obtained.

[ 495]

Intermediate (I-D) (15.0g), bis (4-tert-butylphenyl) amine (25.9g), bis (dibenzylideneacetone) palladium (0.48g), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos, 0.86g), sodium tert-butoxide (10.0g) and xylene (130mL) were placed in a flask under a nitrogen atmosphere, and heated at 100 ℃ for 1 hour. After the reaction, water and toluene were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene), whereby 23.0g of intermediate (I-E) was obtained.

[ 496]

To a flask containing intermediate (I-E) (23.0g) and tert-butylbenzene (250ml) was added 1.62M t-butyllithium pentane solution (33.5ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 60 ℃ and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of tert-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (13.6g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled to 0 ℃ again, N-diisopropylethylamine (7.0g) was added thereto, and after stirring at room temperature until heat generation ended, it was heated to 100 ℃ and stirred with heating for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath was added thereto, followed by ethyl acetate. After the organic layer was concentrated, it was purified by a short column of silica gel (eluent: heated chlorobenzene). The obtained crude product was washed with refluxing heptane and refluxing ethyl acetate, and then reprecipitated from chlorobenzene, whereby compound (2-538) (12.9g) was obtained.

[ 497]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.3(s,18H),1.5(s,18H),5.6(s,2H),6.8(d,2H),7.1(m,4H),7.4～7.5(m,6H),9.0(d,2H).

Synthesis examples (2 to 12): synthesis of Compound (2-541)

[ chemical 498]

Under nitrogen atmosphere, mixing⁵Aniline (5.0g), d ⁵Bromobenzene (8.25g), Pd-132(0.36g) as a palladium catalyst, NaOtBu (7.1g) and xylene (100mL) were placed in a flask and heated at 120 ℃ for 1.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene/heptane 1/1 (volume ratio)), whereby 8.1g of intermediate (I-F) was obtained.

[ 499]

Intermediate (I-F) (8.0G), intermediate (I-G) (20.6G), Pd-132(0.31G) as a palladium catalyst, NaOtBu (6.4G) and xylene (100mL) were placed in a flask under a nitrogen atmosphere, and heated at 120 ℃ for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring, 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 means of a short column of silica gel (eluent: toluene/heptane 1/1 (volume ratio)), whereby 20.0g of intermediate (I-H) was obtained.

[ solution 500]

To a flask containing intermediate (I-H) (10.0g) and tert-butylbenzene (150ml) was added 1.62M t-butyllithium pentane solution (21.2ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 60 ℃ and the mixture was stirred for 0.5 hour, and then the component having a boiling point lower than that of t-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (8.6g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled to 0 ℃ again, N-diisopropylethylamine (4.4g) was added thereto, and after stirring at room temperature until heat generation ended, it was heated to 100 ℃ and stirred with heating for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath was added thereto, followed by ethyl acetate. After the organic layer was concentrated, it was purified by a short column of silica gel (eluent: toluene). The obtained crude product was dissolved in toluene, heptane was added thereto, and the precipitated crystal was filtered, and the crystal separated by filtration was washed with cooled heptane, whereby compound (2-541) (3.1g) was obtained.

[ solution 501]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 13): synthesis of Compound (2-544)

[ solution 502]

Intermediate (I-I) (8.4g), intermediate (I-J) (4.6g), bis (dibenzylideneacetone) palladium (0.23g), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos, 0.32g), sodium tert-butoxide (3.2g) and xylene (40ml) were placed in a flask under a nitrogen atmosphere and heated at 100 ℃ for 1.5 hours. After the reaction, water and toluene were added to the reaction solution, followed by stirring, 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 means of a silica gel short path column (eluent: toluene), whereby intermediate (I-K) (8.6g) was obtained.

[ solution 503]

To a flask containing intermediate (I-K) (8.6g) and tert-butyl benzene (90ml) was added a 1.62M solution of tert-butyllithium pentane (12.9ml) under a nitrogen atmosphere at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 0.5 hour, and then the component having a boiling point lower than that of t-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (5.0g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled to 0 ℃ again, N-diisopropylethylamine (2.6g) was added thereto, and after stirring at room temperature until heat generation ended, it was heated to 100 ℃ and stirred with heating for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath was added, followed by addition of ethyl acetate and stirring 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 in chlorobenzene under heating, and then purified by a silica gel short path column (eluent: heated chlorobenzene). After the obtained crude product was filtered by adding heptane, the crystals were washed with heptane, whereby compound (2-544) (6.5g) was obtained.

[ chemical 504]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 14): synthesis of Compound (2-542)

[ equation 505]

Intermediate (I-I) (10.7g), intermediate (I-D) (6.0g), bis (dibenzylideneacetone) palladium (0.58g), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos, 0.82g), sodium tert-butoxide (4.0g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere and heated at 100 ℃ for 1.5 hours. After the reaction, water and toluene were added to the reaction solution, followed by stirring, separation of the organic layer and washing with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene), and the obtained solid was washed with cooled heptane, whereby intermediate (I-L) (9.4g) was obtained.

[ chemical 506]

To a flask containing intermediate (I-L) (8.6g) and tert-butylbenzene (100ml) was added 1.62M t-butyllithium pentane solution (13.8ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 60 ℃ and the mixture was stirred for 0.5 hour, and then the component having a boiling point lower than that of t-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (5.4g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled to 0 ℃ again, N-diisopropylethylamine (2.8g) was added thereto, and after stirring at room temperature until heat generation ended, it was heated to 100 ℃ and stirred with heating for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath was added, followed by addition of ethyl acetate and stirring 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 in chlorobenzene under heating, and then purified by a silica gel short path column (eluent: heated chlorobenzene). After heptane was added to the obtained crude product and filtration was performed, the crystals were washed with heptane, whereby compound (2-542) (5.9g) was obtained.

[ 507]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.32(s,18H),1.46(s,18H),5.55(s,2H).

Synthesis examples (2 to 15): synthesis of Compound (2-290)

[ solution 508]

The compounds (2 to 290) were synthesized according to the method described in "synthetic example (1)" of International publication No. 2017/126443.

The structure of the obtained compound (2-290) was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 16): synthesis of Compound (2-351)

[ chemical 509]

The compounds (2 to 351) were synthesized according to the method described in "Synthesis example (5)" of International publication No. 2017/126443.

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

¹H-NMR(CDCl₃)：δ＝9.22(s,1H),8.78(s,1H),7.96(d,2H),7.80～7.77(m,6H),7.71(d,1H),7.59～7.44(m,8H),7.39(t,1H),7.32～7.29(m,4H),7.71(d,1H),7.19(dd,4H),7.12～7.06(m,4H),7.00(d,1H),6.45(d,1H),1.57(s,6H).

Further, the glass transition temperature (Tg) of the compound of the formula (2-351) was 165.6 ℃.

[ measurement machine: a delmond (Diamond) Differential Scanning Calorimeter (DSC) (manufactured by PERKIN ELMER); the measurement conditions were as follows: cooling rate of 200 deg.C/Min, heating rate of 10 deg.C/Min

Synthesis examples (2 to 17): synthesis of Compound (2-60)

[ solution 510]

Compound (2-60) was synthesized by the same method as in Synthesis example (2-1).

The structure of the obtained compound was confirmed by NMR measurement.

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 examples (2 to 18): synthesis of Compound (2-561)

[ solution 511]

Compound (2-561) was synthesized in the same manner as in Synthesis example (2-1).

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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 examples (2 to 19): synthesis of Compound (2-574)

[ formulation 512]

Compound (2-574) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-574) by mass spectrometry.

EI-MS：m/z＝756。

Synthesis examples (2 to 20): synthesis of Compound (2-578)

[ chemical 513]

Compound (2-578) was synthesized in the same manner as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-578) by mass spectrometry.

EI-MS：m/z＝889。

Synthesis examples (2 to 21): synthesis of Compound (2-580)

[ solution 514]

Compound (2-580) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-580) by mass spectrometry.

EI-MS：m/z＝811。

Synthesis examples (2 to 22): synthesis of Compound (2-589)

[ solution 515]

Compound (2-589) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-589) by mass spectrometry.

EI-MS：m/z＝944。

Synthesis examples (2 to 23): synthesis of Compound (2-591)

[ solution 516]

Tri-p-tolylamine (0.287g, 1.00mmol), boron triiodide (0.783g, 2.00mmol) and o-dichlorobenzene (10.0ml) were stirred under nitrogen and heated at 150 ℃ for 2 hours. The reaction was cooled to room temperature and 2-isopropenylphenylmagnesium bromide (5.25ml, 1.2M, 6.30mmol) was added. Then, filtration was carried out using a magnesium silicate (Florisil) short-path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was washed with hexane and then subjected to separation and purification to obtain 0.309g of 2, 8-dimethyl-10- (2- (prop-1-en-2-yl) phenyl) -5- (p-tolyl) -5, 10-dihydrodibenzo [ b, e ] [1,4] azaborine in a yield of 75%.

[ 517]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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).

¹³C-NMR(CDCl₃)：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- (prop-1-en-2-yl) phenyl) -5- (p-tolyl) -5, 10-dihydrodibenzo [ b, e ] [1,4] azaborine (82.2mg, 0.20mmol), scandium trifluoromethanesulfonate (0.100g, 0.20mmol) and 1, 2-dichloroethane (55.0ml) were stirred under a nitrogen atmosphere at 95 ℃ for 24 hours. After the reaction solution was cooled to room temperature, it was filtered by using a magnesium silicate short path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was subjected to separation and purification by means of a silica gel column (eluent: hexane/toluene 6/1 (volume ratio)), whereby 32.0mg of compound (2-591) was obtained in 39% yield.

[ solution 518]

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：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).

¹³C-NMR(CDCl₃)：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 examples (2 to 24): synthesis of Compound (2-32)

[ Hua 519]

The compound represented by the formula (2-32) was synthesized by the same method as in synthesis example (2-1). The obtained compound was confirmed to be compound (2-32) by mass spectrometry.

EI-MS：m/z＝645。

Comparative Synthesis example (1)

Synthesis of Compound (H-1)

[ solution 520]

Compound (H-1) is synthesized by appropriately changing the method described in International publication No. 2015/064560.

Comparative Synthesis example (2)

Synthesis of Compound (H-2)

[ chemical 521]

The compound (H-2) is synthesized according to the method described in Japanese patent laid-open No. 2006-045503.

Comparative Synthesis example (3)

Synthesis of Compound (H-3)

[ formulation 522]

Compound (H-3) was synthesized according to the method described in International publication No. 2018/150832.

Comparative Synthesis example (4)

Synthesis of Compound (D-1)

[ 523]

Compound (D-1) was synthesized according to the synthesis of Compound 1 of International publication No. 2012/118164.

The other compounds of the present invention can be synthesized by the methods according to the synthesis examples described above by appropriately changing the starting compounds.

Hereinafter, examples of the organic EL device using the compound of the present invention are shown for describing the present invention in more detail, but the present invention is not limited to these examples.

Organic EL elements of example 1 to example 165, reference example 1 to reference example 10, and comparative example 1 to comparative example 10 were prepared, and each of them was measured for 1000cd/m²The characteristics in light emission include light emission wavelength (nm), voltage (V), and external quantum efficiency (%). The organic EL elements of examples 18 to 60, 79 to 134, 142 to 165, 2 to 3, 5 to 7, 9 to 10, 2 to 3, 5 to 7, 7 and 9 to 10 were measured at 10mA/cm ²The time for which the luminance of 90% or more of the initial luminance is maintained when the constant current driving is performed at the current density of (1) is regarded as the element lifetime (hr).

The quantum efficiency of a light-emitting element includes an internal quantum efficiency and an external quantum efficiency, and the internal quantum efficiency indicates a ratio of external energy injected as electrons (or holes) into a light-emitting layer of the light-emitting element to be converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting element, and since a part of photons generated in the light-emitting layer is absorbed or continuously reflected inside the light-emitting element without being emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring the external quantum efficiency is as follows. Using a voltage/current generator R6144 manufactured by Edwarden (Advantest), the luminance of the applied element became 1000cd/m²The element emits light by the voltage of (3). 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 (TOPCON). Assuming that the light-emitting surface is a perfect diffusion surface, the number obtained by dividing the value of the spectral emission luminance of each measured wavelength component by the wavelength energy and multiplying by pi is the number of photons at each wavelength. Then, the number of photons is integrated over the entire wavelength range to be observed, and the total number of photons emitted from the element is set. Dividing the applied current value by the element charge (elementary charge) to obtain a value as the number of carriers injected into the device, and dividing the total number of photons emitted from the device by the number of carriers injected into the device The number obtained for the number of carriers (c) is the external quantum efficiency.

Table 2 below shows the material composition and EL characteristic data of each layer in the organic EL devices of examples 1 to 17, reference example 1, and comparative example 1.

In each of the tables, "HI" is N⁴,N^4'-diphenyl-N⁴,N^4'-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]-4,4 '-diamine, "HAT-CN" is 1,4,5,8,9, 12-hexaazatriphenylhexacarbonitrile, "HT-1" is N- ([1,1' -biphenyl)]-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, "HT-2" is N, N-bis (4- (dibenzo [ b, d ] s)]Furan-4-yl) phenyl) - [1, 1': 4', 1' -terphenyl]-4-amine, "ET-1" is 4,6,8, 10-tetraphenyl [1, 4]]Benzoxaborole heterocyclohexeno [2,3,4-k1]Phenoxyboron heterocyclic hexene, ET-2, 9- ([1, 4-phenylene) and ET-3, 3' - ((2-phenylanthracene-9, 10-diyl) bis (4, 1-phenylene)) bis (4-methylpyridine)]Benzoxaborole heterocyclohexeno [2,3,4-kl]Phenoxyboron heterocyclic hexen-7-yl) -9H-carbazole, ET-4 is 9- [4- ([1, 4] methyl ethyl ketone]Benzoxaborole heterocyclohexeno [2,3,4-kl]Phenoxyboron heterocyclohexen-7-yl) phenyl]-9H-carbazole. The chemical structure is shown below together with "Liq".

[ solution 524]

< example 1 >

< host material: compounds (1-47), dopant materials: element of Compound (2-41)

A glass substrate (manufactured by Opto Science) having a thickness of 180nm and a thickness of 26mm × 28mm × 0.7mm prepared by polishing ITO to 150nm was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by the Changzhou industry Co., Ltd.), and a boat for vapor deposition of tantalum was set in which HI, HAT-CN, HT-1, HT-2, compound (1-47), compound (2-41), ET-1, and ET-2 were placed, and a boat for vapor deposition of aluminum nitride was set in which Liq, magnesium, and silver were placed.

As shown in table 2, the following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10^-4Pa，HI, HAT-CN, HT-1 and HT-2 were sequentially deposited by evaporation to form a hole injection layer 1 (film thickness: 40nm), a hole injection layer 2 (film thickness: 5nm), a hole transport layer 1 (film thickness: 15nm) and a hole transport layer 2 (film thickness: 10 nm). Then, the compounds (1 to 47) and the compounds (2 to 41) were simultaneously heated and vapor-deposited so that the film thickness became 25nm, thereby forming a light-emitting layer. The deposition rate was adjusted so that the mass ratio of the compounds (1-47) to the compounds (2-41) became approximately 98 to 2. Subsequently, ET-1 was heated and vapor-deposited to a film thickness of 5nm to form the electron transporting layer 1. Then, ET-2 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25nm, thereby forming the electron transporting layer 2. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq became approximately 50 to 50. The deposition rate of each layer is 0.01 nm/sec to 1 nm/sec. Then, Liq was heated and vapor-deposited at a vapor deposition rate of 0.01 nm/second to 0.1 nm/second so that the film thickness became 1nm, and then magnesium and silver were simultaneously heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. In this case, the deposition rate is adjusted between 0.1 nm/sec and 10 nm/sec so that the atomic ratio of magnesium to silver is 10 to 1.

The ITO electrode was used as an anode, a magnesium/silver electrode was used as a cathode, and a DC voltage was applied to the ITO electrode and the magnesium/silver electrode to measure 1000cd/m²As a result of the characteristics in light emission, blue light emission having a wavelength of 461nm and a driving voltage of 4.11V and an external quantum efficiency of 6.32% was obtained as shown in Table 3.

< example 2 to example 17 >

Each organic EL device was manufactured in the layer structure shown in table 2 according to example 1, and EL characteristic data was measured (table 2).

< reference example 1 >

< comparative example 1 >

< example 18 to example 25 >

Each organic EL device was manufactured in the layer structure shown in table 3 according to example 1, and EL characteristic data was measured (table 3).

< reference example 2 >

< example 26 to example 44 >

Each organic EL device was manufactured in accordance with example 1 with the layer structure shown in table 4, and EL characteristic data was measured (table 4).

< comparative example 2 >

< example 45 to example 60 >

Each organic EL device was manufactured in accordance with example 1 with the layer structure shown in table 5, and EL characteristic data was measured (table 5).

< reference example 3 >

< comparative example 3 >

< example 60 to example 78 >

Each organic EL device was manufactured in accordance with example 1 with the layer structure shown in table 6, and EL characteristic data was measured (table 6).

< reference example 4 >

< comparative example 4 >

< example 79 to example 103 >

Each organic EL device was manufactured in accordance with example 1 with the layer structure shown in table 7, and EL characteristic data was measured (table 7).

< reference example 5 >

< comparative example 5 to comparative example 6 >

< example 104 to example 134 >

Each organic EL device was manufactured in the layer structure shown in table 8 according to example 1, and EL characteristic data was measured (table 8).

< reference example 6 to reference example 7 >

< comparative example 7 >

< embodiment 135 to embodiment 141 >

Each organic EL device was manufactured in accordance with example 1 with the layer structure shown in table 9, and EL characteristic data was measured (table 9).

< reference example 8 >

< comparative example 8 >

< example 142 to example 154 >

Each organic EL device was manufactured according to example 1 with the layer structure shown in table 10, and EL characteristic data was measured (table 10).

< reference example 9 >

< comparative example 9 >

< example 155 to example 165 >

Each organic EL element was produced in accordance with example 1 with the layer structure shown in table 11, and EL characteristic data were measured (table 11).

< reference example 10 >

< comparative example 10 >

[ industrial applicability ]

The present invention can provide an organic EL element which has high external quantum efficiency and can emit light at a low voltage.

Claims

1. An organic electroluminescence element comprising a pair of electrodes and a light-emitting layer, the pair of electrodes comprising an anode and a cathode, the light-emitting layer is disposed between the pair of electrodes, and the light-emitting layer comprises a host material An anthracene-based compound represented by the following formula (1), and a polycyclic aromatic compound represented by the following formula (2) as a dopant material, or a compound having a plurality of structures represented by the following formula (2) Multimers of polycyclic aromatic compounds,

In formula (1),

Ar ^c is a substituted aryl or a substituted heteroaryl,

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 each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diaryl arylamino, substituted diheteroarylamino, substituted arylheteroarylamino, substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted alkoxy, aryloxy which may be substituted, arylthio which may be substituted, or silyl which may be substituted,

At least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium,

In formula (2),

Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, at least one hydrogen in these rings may be substituted,

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S or >Se, and R of said >NR is a substituted aryl group, a substituted heteroaryl group , a substituted alkyl group or a substituted cycloalkyl group, the R of the >C(-R) ₂ is hydrogen, a substituted aryl group, a substituted alkyl group or a substituted cycloalkane group In addition, the R of >NR and/or the R of >C(-R) ₂ may be bonded to the A ring, the B ring and/or the C ring through a linking group or a single bond Knot,

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, at least one hydrogen in the cycloalkane may be substituted, and the cycloalkane may be substituted At least one of -CH ₂ - can be substituted by -O-,

At least one hydrogen in the compound or structure represented by formula (2) may be substituted by deuterium, cyano or halogen.

2 . The organic electroluminescence element according to claim 1 , wherein the polycyclic aromatic compound represented by formula (2) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) Or having a plurality of structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) Multimers of polycyclic aromatic compounds,

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 each independently hydrogen, aryl, heteroaryl, diarylamino, Diheteroarylamino, arylheteroarylamino, diarylboronyl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted where the two aryl groups can be linked via a single bond or linking group silyl groups, at least one of which hydrogen can be substituted by aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , Adjacent groups among R ⁷ , R 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, the b ring or the c ring. At least one hydrogen can be aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboronyl where two aryls can be linked via a single bond or linking group, alkane substituted with aryl, cycloalkyl, alkoxy, aryloxy or substituted silyl, at least one of which hydrogen may be substituted with aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl,

X _X is each independently >O, >S, >NR or >C(-R) ₂ , and R of said >NR is a substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkane group or a substituted cycloalkyl group, in addition, the Rs of >C(-R) ₂ are each independently hydrogen, an aryl group that can be substituted by an alkyl group or a cycloalkyl group, an alkyl group that can be substituted by an alkyl group or a cycloalkyl group Heteroaryl, alkyl or cycloalkyl,

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S or >Se, and R of said >NR is an alkyl group having 1 to 6 carbon atoms or an alkyl group having 3 to 3 carbon atoms. Aryl having 6 to 12 carbon atoms substituted by a cycloalkyl group of 14, a heteroaryl group having 2 to 15 carbon atoms that may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, or a heteroaryl group having 1 carbon atoms ~6 alkyl group or cycloalkyl group with 3-14 carbon atoms, the R of >C(-R) ₂ is hydrogen, which can be substituted by an alkyl group with 1-6 carbon atoms or a cycloalkyl group with 3-14 carbon atoms aryl group with 6-12 carbon atoms, alkyl group with 1-6 carbon atoms or cycloalkyl group with 3-14 carbon atoms, in addition, the R of the >NR and/or the >C(-R) ₂ R may be bonded to the a ring, the b ring and/or the c ring through -O-, -S-, -C(-R) ₂ - or a single bond, the -C(-R ) ₂ - R is independently an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

Compounds represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or multimers thereof At least one of the aryl ring and the heteroaryl ring in the cycloalkane can be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane can be substituted, and at least one -CH ₂ - in the cycloalkane can be substituted with -O- ,

At least one of the compounds or structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) One hydrogen can be replaced by deuterium, cyano or halogen,

In the case of polymers, having two or three formulae (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula A dimer or trimer of the structure represented by (2-f).

3. The organic electroluminescence element according to claim 2, wherein the compound represented by the formula (2) is a polycyclic aromatic compound represented by the formula (2-a) or the formula (2-b) or has a plurality of A multimer of a polycyclic aromatic compound having a structure represented by formula (2-a) or formula (2-b).

4. The organic electroluminescence element according to claim 3, wherein the compound represented by the formula (2) is any one of the compounds represented by the following formula,

5. The organic electroluminescence element according to any one of claims 1 to 4, wherein in formula (1),

Any two of Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ and Ar ¹⁸ are substituted aryl groups or substituted heteroaryl groups, and the other six are hydrogen , which may be substituted alkyl, which may be substituted cycloalkyl, which may be substituted alkenyl, or which may be substituted alkoxy.

6. The organic electroluminescence element according to claim 5, wherein the anthracene-based compound represented by the formula (1) is the following formula (1A), formula (1B), formula (1C), formula (1D) or formula The anthracene-based compound represented by (1E),

In formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E),

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ' and Ar ¹⁸ ' are each independently phenyl, biphenyl, terphenyl, tetraphenyl , naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group or group represented by formula (A), at least one hydrogen in these groups can be phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl , benzofluorenyl,

group, triphenylene group, pyrenyl group, or group represented by the formula (A), and here, when both hydrogens of the methylene group in the fluorenyl group and the benzofluorenyl group are substituted with phenyl groups, these phenyl groups are mutually substituted with each other. can be bonded with a single key,

A methyl group or a tertiary group may be bonded to a carbon atom on an anthracene ring that is not bonded to Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ' or Ar ¹⁸ ' butyl instead of hydrogen,

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

The group represented by the formula (A) is a group obtained by removing one hydrogen at an arbitrary position of the formula (A), and * represents the position,

In formula (A), Y is -O-, -S- or >NR ³⁹ , and R ²¹ to R ²⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted Aryl, heteroaryl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dioxane cycloalkylsilyl group, alkylbicycloalkylsilyl group, substituted amino group, halogen, hydroxyl or cyano group, the adjacent groups in R ²¹ to R ²⁸ can be bonded to each other to form a hydrocarbon ring, an aryl ring or heteroaryl ring, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted alkyl group, substituted cycloalkyl group, substituted aryl group, substituted Substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilane , alkylbicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano substituted, R ³⁹ is hydrogen or optionally substituted aryl.

7. The organic electroluminescent element according to claim 6, wherein

The group represented by the formula (A-1) to the formula (A-14) is a group obtained by removing one hydrogen at any position of the formula (A-1) to the formula (A-14), and * represents the position,

In formula (A-1) to formula (A-14), Y is -O-, -S- or >NR ³⁹ , R ³⁹ is hydrogen or aryl, formula (A-1) to formula (A-14) At least one hydrogen in the represented group can be selected from alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dicycloalkylsilyl Alkylcycloalkylsilyl, alkylbicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, hydroxy or cyano replace,

8. The organic electroluminescent element according to claim 6 or 7, wherein

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ' and Ar ¹⁸ ' are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthrene group, fluorenyl group, or group represented by any one of formula (A-1) to formula (A-4), at least one hydrogen in these groups may be phenyl, biphenyl, naphthyl, phenanthryl, fluorene substituted by a group or a group represented by any one of formula (A-1) to formula (A-4),

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

9. The organic electroluminescence element according to claim 5, wherein Ar ¹⁴ and Ar ¹⁵ are substituted aryl groups or substituted heteroaryl groups, Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ¹⁷ and Ar ¹⁸ are both hydrogen.

10 . The organic electroluminescence element according to claim 9 , wherein at least one selected from the group consisting of Ar ^c , Ar ¹⁴ and Ar ¹⁵ is a group including an anthracene ring. 11 .

11. The organic electroluminescent element according to claim 9, wherein at least one selected from the group consisting of Ar ^c , Ar ¹⁴ and Ar ¹⁵ comprises a group represented by formula (A'),

In formula (A'), R ²¹ to R ²⁸ are each independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted Substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkyl Silyl group, substituted amino group, halogen, hydroxyl or cyano group, adjacent groups in R ²¹ to R ²⁸ can be bonded to each other to form a hydrocarbon ring, aryl ring or heteroaryl ring, the formed hydrocarbon ring, aryl At least one hydrogen in the base ring or the heteroaryl ring can be substituted alkyl, cycloalkyl, aryl, heteroaryl, alkoxy , aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, which may be Substituted amino, halo, hydroxy or cyano substitution.

12. The organic electroluminescence element according to claim 9, wherein at least one hydrogen in the compound represented by formula (1) is substituted with deuterium.

13. The organic electroluminescence element according to any one of claims 1 to 12, comprising an electron transport layer and/or an electron injection layer disposed between the cathode and the light-emitting layer, the electron transport layer and at least one layer of the electron injection layer contains borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives , aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and oxazoline at least one of the group consisting of derivatives.

14. The organic electroluminescence element according to claim 13, wherein the electron transport layer and/or the electron injection layer further contains a compound selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halogenated alkali metals compounds, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals at least one of the groups.

15. A display device comprising the organic electroluminescence element according to any one of claims 1 to 14.

16. A lighting device comprising the organic electroluminescent element according to any one of claims 1 to 14.

17. An anthracene-based compound represented by the following formula (1):

In formula (1),

Ar ^c is a substituted aryl or a substituted heteroaryl,

R ^c is hydrogen, alkyl or cycloalkyl,

At least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium.

18. The anthracene-based compound according to claim 17, which is represented by the following formula (1Aa):

In formula (1Aa), Ar ^c ', Ar ¹⁴ ' and Ar ¹⁵ ' are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrene group, or group represented by any one of formula (A-1) to formula (A-14), at least one hydrogen in these groups may be phenyl, biphenyl, terphenyl , tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group, or group represented by any one of formula (A-1) to formula (A-14), here, when the methylene group in the fluorenyl group and the benzofluorenyl group is substituted When all hydrogens are replaced by phenyl groups, these phenyl groups can be bonded to each other through a single bond, and a methyl group or a tertiary group can be bonded to the carbon atom on the anthracene ring to which Ar ^c ', Ar ¹⁴ ' or Ar ¹⁵ ' is not bonded. butyl instead of hydrogen,

At least one hydrogen in the compound represented by formula (1Aa) may be substituted by halogen, cyano or deuterium,

Wherein, at least one hydrogen in the compound represented by formula (1Aa) may be substituted by halogen or cyano, and at least one hydrogen in the compound represented by formula (1Aa) may be substituted by deuterium.

19. The anthracene-based compound according to claim 18, wherein Ar ^c ', Ar ¹⁴ ' and Ar ¹⁵ ' are independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or A group represented by any one of formula (A-1) to formula (A-4), at least one hydrogen in these groups may be phenyl, naphthyl, phenanthryl, fluorenyl, or formula (A-1) to The group represented by any one of formula (A-4) is substituted.

20. The anthracene-based compound according to claim 18 or 19, wherein in formula (1Aa), at least the hydrogen bonded to the 10-position of the anthracene ring is substituted with deuterium.

21. The anthracene-based compound according to claim 18, which is represented by the following arbitrary formula:

In the formula, D represents deuterium.

22. The anthracene-based compound according to claim 17, which is represented by any of the following formulas:

In the formula, D represents deuterium.

23. The anthracene-based compound according to claim 17, which is represented by the following arbitrary formula:

24. The anthracene-based compound according to claim 17, which is represented by any of the following formulas:

In the formula, D represents deuterium.

25. The anthracene-based compound according to claim 17, which is represented by the following arbitrary formula:

In the formula, D represents deuterium.

26. The anthracene-based compound according to claim 17, which is represented by any of the following formulas:

In the formula, Me represents a methyl group, tBu represents a tert-butyl group, and CyHex represents a cyclohexyl group.

27. The anthracene-based compound according to claim 17, which is represented by the following arbitrary formula:

In the formula, D represents deuterium.