Organic electroluminescent element and anthracene-based compound

Abstract

To provide an organic EL element having a high external quantum efficiency.SOLUTION: An organic electroluminescent element 100 comprises: a pair of electrodes composed of a positive electrode 102 and a negative electrode 108; and a luminescent layer 105 disposed between the pair of electrodes. The luminescent layer contains: an anthracene-based compound represented by the formula (1) below as a host material; and as a dopant material, a polycyclic aromatic compound represented by the formula (2) below or a multimer thereof.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an organic electroluminescent element, a display device, and a lighting device using the same. The present invention also relates to an anthracene-based compound that can be used as a light-emitting material.

Background Art

[0002] Conventionally, display devices using light-emitting elements that emit light by an electric field have been variously studied because they can achieve power saving and thinning. Furthermore, organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") made of organic materials have been actively studied because they can be easily made lighter and larger. 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 that provide optimal light-emitting characteristics have been actively studied so far, regardless of whether they are polymer compounds or low-molecular compounds.

[0003] An organic EL element has a structure including a pair of electrodes composed of an anode and a cathode, and one or a plurality of layers containing an organic compound disposed between the pair of electrodes. The layer containing the organic compound includes a light-emitting layer, a charge transport / injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] Patent Document 1 describes the use of an anthracene-based compound as a light-emitting material for 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 Documents

[0005]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0006] As described above, various materials have been developed for use in organic EL elements. However, in order to increase the options for materials for organic EL elements, the development of materials composed of compounds different from the conventional ones is desired. An object of the present invention is to provide an organic EL element using a new combination of materials. Another object of the present invention is to provide an organic EL element having a high external quantum efficiency.

Means for Solving the Problems

[0007] As a result of intensive studies to solve the above problems, the present inventors have found that an excellent organic EL element can be obtained by using a light-emitting layer containing a specific anthracene-based compound as a host material and a polycyclic aromatic compound having a plurality of condensed aromatic rings as a dopant material, and have completed the present invention. That is, the present invention provides the following organic electroluminescent elements and anthracene-based compounds.

[0008] <1> An organic electroluminescent element having a pair of electrodes composed of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains an anthracene-based compound represented by the following formula (1) as a host material, and a polycyclic aromatic compound represented by the following formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2) as a dopant material.

[0009]

Chemical formula

[0010] In formula (1), Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, R c is hydrogen, alkyl, or cycloalkyl, Ar 11 、Ar12 、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 diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

[0011] In formula (2), Ring A, Ring B, and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted, X 1 and X 2 are each independently >O, >N-R, >C(-R) 2 、>S, or >Se, wherein R of the >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R of the >C(-R) 2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and further, R of the >N-R and / or R of the >C(-R) 2 may be bonded to the Ring A, Ring B, and / or Ring C by a linking group or a single bond, In the compound represented by formula (2) or its multimer, at least one of the aryl ring and the heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - in the cycloalkane may be substituted with -O-; At least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or halogen.

[0012] <2> The organic electroluminescent device according to <1>, wherein the polycyclic aromatic compound represented by formula (2) or the multimer of the polycyclic aromatic compound 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 a multimer of a polycyclic aromatic compound 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);

[0013] [Chemical formula]

[0014] 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 11is, independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 among them, adjacent groups may combine with each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring, or c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, X X is, independently of one another, >O, >S, >N-R, or >C(-R) 2 wherein R of the >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and also, R of the >C(-R) 2 is, independently of one another, hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, X 1 and X 2is, independently, >O, >N-R, >C(-R) 2 , >S, or >Se, wherein R in said >N-R is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and R in said >C(-R) 2 is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and further, R in said >N-R and / or R in said >C(-R) 2 may be bonded to the a-ring, b-ring, and / or c-ring by -O-, -S-, -C(-R) 2 -, or a single bond, and R in said -C(-R) 2 is, independently, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, In the compound or its multimer represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), at least one of the aryl ring and the heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in said cycloalkane may be substituted, and at least one -CH 2 - in said cycloalkane may be substituted with -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 a multimer, it is a dimer or trimer 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).

[0015] <3> The organic electroluminescent device 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 polycyclic aromatic compound having a plurality of structures represented by formula (2-a) or formula (2-b).

[0016] <4> The organic electroluminescent device according to <3>, wherein the compound represented by formula (2) is any of the compounds represented by the following formulas;

Chem.

[0017]

Chem.

[0018]

Chem.

[0019] <5> In formula (1) Ar 11 、Ar 12 、Ar 13 、Ar 14 、Ar 15 、Ar 16 、Ar 17 、and Ar 18 are each independently optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. The organic electroluminescent device according to any one of <1> to <4>.

[0020] <6> The organic electroluminescent device according to <5>, wherein the anthracene-based compound represented by formula (1) is an anthracene-based compound represented by the following formula (1A), (1B), (1C), (1D), or (1E); [Chemical formula]

[0021] In formula (1A), (1B), (1C), (1D) or (1E), Ar c ’, Ar 11 ’, Ar 12 ’, Ar 13 ’, Ar 14 ’, Ar 15 ’, Ar 17 ’, and Ar 18 ’ are each independently phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when both hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Ar c ’, Ar 11 ’, Ar 12 ’, Ar 13 ’, Ar 14 ’, Ar 15 ’, Ar 17 ’, or Ar 18 ’ may be bonded to the carbon atom on the anthracene ring to which it is not bonded with methyl or t-butyl in place of hydrogen. At least one hydrogen in the compound represented by formula (1A), (1B), (1C), (1D) or (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 * indicates that position. In formula (A), Y is -O-, -S- or >N-R 39 where R21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and R 21 ~R 28 Among them, 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 in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano, and R 39 is hydrogen or optionally substituted aryl.

[0022] <7> The group represented by formula (A) is a group represented by any one of formulas (A-1) to (A-14), The groups represented by formulas (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of each of formulas (A-1) to (A-14), and * indicates that position, In formulas (A-1) to (A-14), Y is -O-, -S-, or >N-R 39 and R 39is hydrogen or aryl, and at least one hydrogen in the group represented by formula (A-1) to formula (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano. The organic electroluminescent device according to <6>.

[0023]

Chemical formula

[0024] <8> Ar c ’, Ar 11 ’, Ar 12 ’, Ar 13 ’, Ar 14 ’, Ar 15 ’, Ar 17 ’, and Ar 18 ’ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of formula (A-1) to formula (A-4), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of formula (A-1) to formula (A-4). At least one hydrogen in the compound represented by formula (1A), (1B), (1C), (1D) or (1E) may be substituted with halogen, cyano, or deuterium. The organic electroluminescent device according to <6> or <7>.

[0025] <9>Ar 14 , Ar 15 is optionally substituted aryl or optionally substituted heteroaryl, and Ar 11 , Ar 12 , Ar 13 , Ar 16, Ar 17 and Ar 18 are both hydrogen, the organic electroluminescent device according to <5>. <10>Ar C , Ar 14 , and Ar 15 at least one selected from the group consisting of is a group containing an anthracene ring, the organic electroluminescent device according to <9>.

[0026] <11>Ar C , Ar 14 , and Ar 15 at least one selected from the group consisting of contains a group represented by formula (A’), the organic electroluminescent device according to <9>;

Chemical formula

[0027] In formula (A’), R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and R 21 ~R 28Among them, 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 in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with 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, alkyldicycloalkylsilyl, amino which may be substituted, halogen, hydroxy, or cyano.

[0028] <12>The organic electroluminescent device according to <9>, wherein at least one hydrogen in the compound represented by formula (1) is substituted with deuterium. <13>The organic electroluminescent device 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, and at least one of the electron transport layer and the electron injection layer contains 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, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

[0029] <14>The organic electroluminescent device 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> An illumination device comprising the organic electroluminescent element according to any one of <1> to <14>.

[0030] <17> An anthracene compound represented by the following formula (1);

Chemical formula

[0031] In formula (1), Ar c is optionally substituted aryl or optionally 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 diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

[0032] <18> The anthracene compound according to <17>, represented by the following formula (1Aa);

Chemical formula

[0033] In formula (1Aa), Ar c ’, Ar 14 ’, and Ar 15 ’ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-14), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-14). Here, when all the hydrogens of the methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Ar c ’, Ar 14 ’, or Ar 15 ’ is not bonded, a methyl or t-butyl may be bonded in place of hydrogen to the carbon atom on the anthracene ring At least one hydrogen in the compound represented by formula (1Aa) may be substituted with halogen, cyano, or deuterium The groups represented by formulas (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of each of formulas (A-1) to (A-14), and * indicates that position In formulas (A-1) to (A-14), Y is -O-, -S-, or >N-R 39 wherein R 39 is hydrogen or aryl, and at least one hydrogen in the groups represented by formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano However, at least one hydrogen in the compound represented by the formula (1Aa) may be substituted with a halogen or cyano, and at least one hydrogen in the compound represented by the formula (1Aa) is substituted with deuterium.

[0034] <19> Ar c’ , Ar 14 ’ and Ar 15 ’ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the formulas (A-1) to (A-4), and at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the formulas (A-1) to (A-4), the anthracene-based compound according to <18>. <20> In the formula (1Aa), at least the hydrogen bonded to the 10-position of the anthracene ring is substituted with deuterium, the anthracene-based compound according to <18> or <19>.

[0035] <21> The anthracene-based compound according to <18> represented by any one of the following formulas.

Chemical formula

[0036]

Chemical formula

[0037]

Chemical formula

[0038]

Chemical formula

[0039] <22> The anthracene-based compound according to <17> represented by any one of the following formulas. [Chemistry]

[0040] [Chemistry]

[0041] [Chemistry] [Chemistry]

[0042] [Chemistry]

[0043] [Chemistry]

[0044] [Chemistry] (In the above formula, D represents deuterium.)

[0045] <23> The anthracene-based compound according to <17>, which is represented by any of the following formulas. [Chemistry]

[0046] [Chemistry]

[0047] [Chemistry]

[0048] [Chemistry]

[0049] <24> The anthracene compound described in <17> represented by any of the following formulas.

Chemical formula

[0050]

Chemical formula

[0051]

Chemical formula

[0052]

Chemical formula

[0053] <25> The anthracene compound described in <17> represented by any of the following formulas.

Chemical formula

[0054]

Chemical formula

[0055] <26> The anthracene compound described in <17> represented by any of the following formulas.

Chemical formula

[0056] <27> The anthracene compound described in <17> represented by any of the following formulas. [Chemical formula]

[0057] [Chemical formula] (In the above formula, D represents deuterium.) [Advantages of the Invention]

[0058] The present invention provides an organic EL device using a new combination of materials. The organic EL device of the present invention has a high external quantum efficiency and can emit light at a low voltage. Further, the present invention provides an anthracene-based compound that can be used in the production of the above organic EL device. [Brief Description of the Drawings]

[0059]

Figure 1

[0060] Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. Further, in the description of the structural formula in this specification, "hydrogen" means "hydrogen atom (H)".

[0061] In this specification, chemical structures and substituents may be represented by the number of carbon atoms. However, when a substituent is substituted on a chemical structure, or when a further substituent is substituted on a substituent, the number of carbon atoms means the number of carbon atoms of each of the chemical structure and the substituent, and does not mean the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituent and the substituent. For example, "substituent B having Y carbon atoms substituted with substituent A having X carbon atoms" means that "substituent A having X carbon atoms" substitutes "substituent B having Y carbon atoms", and Y is not the total number of carbon atoms of substituent A and substituent B. Another example, "substituent B having Y carbon atoms substituted with substituent A" means that "(substituent A without carbon atom limitation) substituent A" substitutes "substituent B having Y carbon atoms", and Y is not the total number of carbon atoms of substituent A and substituent B.

[0062] <<Organic electroluminescent element>> The organic electroluminescent element of the present invention has a pair of electrodes composed of 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 the organic EL element of the present invention.

[0063] The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0064] Note that the organic EL element 100 may have a configuration in which the manufacturing order is reversed, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, the electron transport layer 106 provided on the electron injection layer 107, the light-emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light-emitting layer 105, the hole injection layer 103 provided on the hole transport layer 104, and the anode 102 provided on the hole injection layer 103.

[0065] Not all of the above layers are essential. With the minimum structural unit consisting of the anode 102, the light-emitting layer 105, and the cathode 108, the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are optional layers. Also, each of the above layers may consist of a single layer or multiple layers.

[0066] As aspects of the layers constituting the organic EL element, in addition to the above-described configuration of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", there may be configurations such as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron 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 transport layer / cathode", "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0067] 1. Light-emitting layer in an organic electroluminescent device The light-emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As the material for forming the light-emitting layer 105, any compound (light-emitting compound) that is excited by the recombination of holes and electrons to emit light may be used, and it is preferable that the compound can form a stable thin film shape and exhibits strong light emission (fluorescence) efficiency in the solid state.

[0068] As the light-emitting mechanism of an organic EL element, there are mainly two types: fluorescence emission using light emission from the singlet excited state and phosphorescence emission using light emission from the triplet excited state. In general, the exciton utilization efficiency of a common fluorescence emission material is low, at most 25%. However, using the phenomenon of singlet exciton generation from multiple triplet excitons (triplet-triplet fusion (TTF)), up to 40 - 62.5% of the energy can be utilized for light emission.

[0069] The generation of singlet excitons from triplet excitons can occur in two ways: on the host material molecules and on the dopant material molecules. At this time, it is preferable that the triplet energy level of the dopant material is higher than the triplet energy level of the host material. When this relationship of the triplet energy levels is satisfied, the triplet excitons generated on the host material do not move to the dopant material with a higher triplet energy. Also, the triplet excitons generated on the dopant material molecules quickly transfer energy to the host material molecules. That is, without the triplet excitons of the host material moving to the dopant material, singlet excitons are efficiently generated by the collision of triplet excitons on the host material. Furthermore, when the singlet energy level of the dopant material is lower than the singlet energy level of the host material, the singlet excitons generated by the TTF phenomenon quickly transfer energy from the host material to the dopant material and contribute to the fluorescent light emission of the dopant material. Also, the energy transfer from the host to the dopant at this time is Förster-type energy transfer. Generally, in an organic EL element, it is known that high-efficiency Förster-type energy transfer occurs when the overlap integral of the fluorescence spectrum of the host and the absorption spectrum of the dopant is large and the host and the dopant are close and have an appropriate orientation.

[0070] By using the host material which is an anthracene-based compound represented by formula (1) of the present invention and the dopant material which is a polycyclic aromatic compound having boron represented by formula (2), it becomes possible to design a material and an element that satisfy the appropriate energy level relationship between the host and the dopant described above and the conditions under which highly efficient Förster-type energy transfer occurs. As a result, in the light-emitting layer of the present invention, the TTF phenomenon can be efficiently generated, and good device characteristics can be provided.

[0071] The light-emitting layer of the organic electroluminescent device of the present invention contains an anthracene-based compound represented by formula (1) as a host material and a polycyclic aromatic compound represented by formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2) as a dopant material.

[0072] 1-1-1. Anthracene-based compound The anthracene-based compound contained in the light-emitting layer of the organic EL device of the present invention is a compound represented by the following formula (1).

Chemical formula

[0073] In formula (1), Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, and R c is hydrogen, alkyl, or cycloalkyl, and Ar 11 、Ar 12 、Ar 13 、Ar 14 、Ar 15 、Ar 16 、Ar 17 、and Ar 18Each is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, and at least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

[0074] Examples of the "aryl" in the "optionally substituted aryl" in formula (1) include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0075] Specific examples of "aryl" include phenyl which is a monocyclic system, biphenylyl which is a bicyclic system, naphthyl which is a condensed bicyclic system, terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl) which is a tricyclic system, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl which are condensed tricyclic systems, triphenylenyl, pyrenyl, naphthacenyl, benzofluorenyl which are condensed tetracyclic systems, perylenyl, pentacenyl which are condensed pentacyclic systems, etc. In this specification, when "fluorenyl" is mentioned, it means fluorenyl or a compound in which one or two of the two hydrogens of the methylene of fluorenyl are substituted with methyl. Also, when "benzofluorenyl" is mentioned, it means benzofluorenyl or a compound in which one or two of the two hydrogens of the methylene of benzofluorenyl are substituted with methyl.

[0076] In formula (1), examples of the "heteroaryl which may be substituted" in the "heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Further, examples of the heteroaryl include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0077] Specific examples of the "heteroaryl" include, for example, 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, cinnolyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naphthobenzofuranyl, naphthobenzothienyl, and the like.

[0078] In each of the "diaryl amino which may be substituted", "diheteroaryl amino which may be substituted", and "aryl heteroaryl amino which may be substituted" in formula (1), the aryl and heteroaryl described above as the "aryl" and "heteroaryl" can be cited.

[0079] Specifically, diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like can be cited.

[0080] In formula (1), the "alkyl" in "alkyl" and "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is still more preferred, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0081] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

[0082] In formula (1), the "cycloalkyl" in "cycloalkyl" and "optionally substituted cycloalkyl" includes, for example, cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms is preferred, cycloalkyl having 3 to 16 carbon atoms is more preferred, cycloalkyl having 3 to 14 carbon atoms is still more preferred, cycloalkyl having 5 to 10 carbon atoms is still more preferred, cycloalkyl having 5 to 8 carbon atoms is particularly preferred, and cycloalkyl having 5 to 6 carbon atoms is most preferred.

[0083] Specific cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their C1-C4 alkyl (especially methyl) substituents, 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, diamantyl, decahydronaphthalenyl, decahydroazulenyl, etc.

[0084] Examples of the "alkenyl" in the "optionally substituted alkenyl" in formula (1) include linear alkenyls having 2 to 24 carbon atoms or branched alkenyls having 4 to 24 carbon atoms. Alkenyls having 2 to 18 carbon atoms are preferred, alkenyls having 2 to 12 carbon atoms are more preferred, alkenyls having 2 to 6 carbon atoms are even more preferred, and alkenyls having 2 to 4 carbon atoms are particularly preferred. Specific examples of the "alkenyl" include vinyl, allyl, butadienyl, etc.

[0085] Examples of the "alkoxy" in the "optionally substituted alkoxy" in formula (1) include linear alkoxys having 1 to 24 carbon atoms or branched alkoxys having 3 to 24 carbon atoms. Alkoxys having 1 to 18 carbon atoms (branched alkoxys having 3 to 18 carbon atoms) are preferred, alkoxys having 1 to 12 carbon atoms (branched alkoxys having 3 to 12 carbon atoms) are more preferred, alkoxys having 1 to 6 carbon atoms (branched alkoxys having 3 to 6 carbon atoms) are even more preferred, and alkoxys having 1 to 4 carbon atoms (branched alkoxys having 3 to 4 carbon atoms) are particularly preferred.

[0086] Specific examples of the "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, etc.

[0087] In formula (1), the "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is substituted with an aryl, and the aryl can be cited as the one described above as the "aryl".

[0088] In formula (1), the "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is substituted with an aryl, and the aryl can be cited as the one described above for Ar 4 and the "aryl" described for X.

[0089] In formula (1), examples of the "optionally substituted silyl" include trialkylsilyl. Examples of the "trialkylsilyl" include those in which the three hydrogens in the silyl are each independently substituted with an alkyl, and the alkyl can be cited as the one described above for Ar 4 and the "alkyl" described for X. Preferred alkyls for substitution are alkyls having 1 to 4 carbon atoms, specifically including methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, cyclobutyl, and the like.

[0090] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, s-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, s-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and the like.

[0091] Ar in formula (1) c 、Ar 11 、Ar 12 、Ar 13 、Ar 14 、Ar 15 、Ar 16 、Ar 17 、and Ar 18 When it is said "optionally substituted" for Ar, Ar, Ar, Ar, Ar, Ar, Ar, Ar, Ar, Ar, and Ar, examples of the substituent include alkyl, aryl, or heteroaryl. As this alkyl, aryl, or heteroaryl, those described above as "alkyl", "aryl", and "heteroaryl" can be cited. The number of substituents may be any number up to the maximum substitutable number, preferably 0 to 3, more preferably 0 to 2, still more preferably 0 to 1. When there are a plurality of substituents, the plurality of substituents may be bonded to each other. For example, when all of the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond.

[0092] Preferable examples of the "optionally substituted aryl" include groups represented by any of the following formula (1-X1) to formula (1-X7).

[0093]

Chemical formula

[0094] In formula (1-X1) to formula (1-X7), * indicates the bonding position. In formula (1-X1) to formula (1-X3), Ar 21 、Ar 22 、and Ar 23 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A) described below.

[0095] In Formula (1-X4) to Formula (1-X7), Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A) described below.

[0096] In Formula (1-X1) to Formula (1-X7), when Ar 21 Ar 22 Ar 23 Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28 is anthracenyl, at least one hydrogen in the anthracenyl may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) described below.

[0097] Also, any one or two or more hydrogens in each of the groups represented by Formula (1-X1) to Formula (1-X7) may be substituted with an alkyl having 1 to 6 carbon atoms (preferably methyl or t-butyl).

[0098] Furthermore, preferred examples of the "optionally substituted aryl" include terphenylyl (particularly, m-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and a group represented by formula (A) described below.

[0099] Examples of the "optionally substituted heteroaryl" also include a group represented by any of formula (A), formula (B), formula (C), formula (D), and formula (E) described below.

[0100] In addition, as the "aryl which may be substituted" or "heteroaryl which may be substituted", a group in which an aryl or heteroaryl is bonded to a carbon atom adjacent to the carbon atom at the bonding position of the group is given as a preferred example. Specifically, it is a group represented by the following formula (1-XB), and the group represented by the formula (1-X6) is an example of the group represented by the formula (1-XB).

[0101]

Chemical formula

[0102] In formula (1-XB), Ar B1 is aryl which may have a substituent or heteroaryl which may have a substituent, the benzene ring to which Ar B1 is bonded may be condensed with another aryl ring or heteroaryl ring to form a condensed ring, Ar B2 is aryl which may have a substituent or heteroaryl which may have a substituent, Ar B2 is bonded to any ring-constituting atom of the benzene ring or the condensed ring, n is an integer of 0 to 2, and when n is 2, a plurality of Ar B2 may be the same or different. The dotted line indicates the skeleton of an aryl ring or heteroaryl ring that forms a condensed ring together with the benzene ring, and * indicates the bonding position of the group represented by the formula (1-XB). In the formula (1-XB), the substituent when "may have a substituent" is aryl or heteroaryl. The formula (1-XB) preferably has at least one condensed ring. For example, the benzene ring to which Ar B1 is bonded is condensed with another aryl ring or heteroaryl ring to form a condensed ring, or Ar B1 or one or more Ar B2 preferably contain a condensed ring. Examples of the condensed ring include a naphthalene ring, a phenanthrene ring, a triphenylene ring, a dibenzofuran ring and the like. The formula (1-XB) preferably has at least one condensed ring and n is 1.

[0103] For example, Ar 14 and Ar 15 may each be an optionally substituted aryl or an optionally substituted heteroaryl, and Ar 11 and Ar 12 and Ar 13 and Ar 16 and Ar 17 and Ar 18 are each hydrogen, and at least one selected from the group consisting of Ar C and Ar 14 and Ar 15 is a group represented by formula (1-XB), the anthracene compound is one of the preferred embodiments. At this time, R c is preferably hydrogen.

[0104] Specific examples include the 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), (1-4112).

[0105] The anthracene-based compound represented by formula (1) preferably has a substituent containing an anthracene ring as "optionally substituted aryl" or "optionally substituted heteroaryl". For example, Ar 14 、Ar 15 is optionally substituted aryl or optionally substituted heteroaryl, and when Ar 11 、Ar 12 、Ar 13 、Ar 16 、Ar 17 and Ar 18 are all hydrogen, it is also preferable that at least one selected from the group consisting of Ar C 、Ar 14 、and Ar 15 is a group containing an anthracene ring. At this time, it is preferable that R c is hydrogen.

[0106] Examples of the group containing an anthracene ring include optionally substituted anthracenyl, any of formulas (1-X1) to (1-X7), and in these formulas, Ar 21 、Ar 22 、Ar 23 、Ar 24 、Ar 25 、Ar 26 、or Ar 27 and / or Ar 28 is a group that is optionally substituted anthracenyl, and a group represented by formula (A) described below, in which any one or two selected from the group consisting of R 21 ~R 28 and R 39 is optionally substituted anthracenyl, etc. Examples of such anthracene-based compounds represented by formula (1) include compounds represented by any of the following formulas.

[0107]

Chemical formula

[0108] In the above formulas, each X is independently an aryl which may be substituted with an aryl or heteroaryl, or a heteroaryl which may be substituted with an aryl or heteroaryl, and each A is independently a single bond, an arylene which may be substituted with an aryl or heteroaryl, or a heteroarylene which may be substituted with an aryl or heteroaryl. Here, for the aryl and heteroaryl, reference can be made to the descriptions of the aryl and heteroaryl in Ar in formula (1). c For the aryl and heteroaryl in c etc., reference can be made to their respective descriptions.

[0109] Preferred examples of the aryl in X of the above formulas include phenyl, 1-naphthyl, 2-naphthyl, etc., and a preferred example of the heteroaryl is the group represented by formula (A). X is preferably an unsubstituted aryl or unsubstituted heteroaryl, and when having a substituent, it is preferably substituted with 1 or 2 phenyl groups.

[0110] As the arylene and heteroarylene in A of the above formulas, in formula (1), Ar c etc., divalent groups obtained by removing any hydrogen from the groups respectively described as the aryl and heteroaryl can be given. Preferred groups include 1,3-phenylene, 1,4-phenylene, 1,6-naphthylene, 2,5-naphthylene, 2,6-naphthylene, 2,7-naphthylene, divalent groups obtained by removing any hydrogen from the group represented by formula (A), etc. A is preferably an unsubstituted arylene or unsubstituted heteroarylene, and when having a substituent, it is preferably substituted with 1 or 2 phenyl groups.

[0111] Specific examples include the compounds represented by the following formula numbers in Table 1: (1-2495), (1-2404), (1-2440), (1-2499), (1-2413), (1-2516), (1-2519), (1-2525), (1-2541), (1-2557), (1-2573), (1-2586), (1-2694), (1-2599), (1-2728), (1-2579), (1-2696), (1-2738), (1-2743), (1-2699), (1-2756), (1-2627), (1-2757), (1-2686), (1-2615), (1-2640), (1-2747), (1-2641), (1-2775), (1-2779), (1-2787), (1-2776), (1-2812), (1-3914), (1-3951), (1-3903), (1-2416), (1-2520), (1-2603), (1-3953), (1-3875).

[0112] In addition, specific examples of the "optionally substituted aryl" and "optionally substituted heteroaryl" include each substituent represented by the structural formula described later as the explanation of the symbols in Table 1.

[0113] At least one hydrogen in the compound represented by formula (1) may be substituted with a halogen, cyano, or deuterium. Examples of the "halogen" in this case include fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogens in the compound represented by formula (1) are substituted with deuterium is preferred.

[0114] Ar 14 , Ar 15 is optionally substituted aryl or optionally substituted heteroaryl, and Ar 11 , Ar 12 , Ar 13 , Ar 16 , Ar 17 and Ar 18 In the compound represented by formula (1) in which all of them are hydrogen, a compound in which at least one hydrogen is substituted with deuterium is preferred. At this time, the substitution position of deuterium is not limited. For example, at least Rc A compound in which is deuterium, Ar c and Ar 11 ~Ar 18 Examples include compounds in which at least one hydrogen in at least one selected from the group consisting of is substituted with deuterium, or compounds in which all hydrogens are substituted with deuterium.

[0115] In formula (1), R c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen.

[0116] On the other hand, Ar 14 , Ar 15 is optionally substituted aryl or optionally substituted heteroaryl, and when Ar 11 , Ar 12 , Ar 13 , Ar 16 , Ar 17 and Ar 18 are all hydrogen, anthracene compounds in which R c is alkyl or cycloalkyl can also be given as preferred examples. Specific examples include the compounds represented by the following formula numbers in Table 1: (1-4434), (1-4429), (1-4458), (1-4409), (1-4404), (1-4427).

[0117] In formula (1), it is preferable that at least two of Ar 11 ~Ar 18 are optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (1) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0118] The anthracene compound represented by formula (1) has Ar 11 ~Ar 18Two of them may be substituted aryl or optionally substituted heteroaryl, and the other six are more preferably hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, the anthracene-based compound represented by the formula (1) more preferably has a structure in which substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring at three positions.

[0119] In the anthracene-based compound represented by the formula (1), two of Ar 11 ~Ar 18 are each independently optionally substituted aryl or optionally substituted heteroaryl, and the other six are each independently hydrogen, methyl, or t-butyl. It is even more preferable that two of Ar 11 ~Ar 18 are each independently optionally substituted aryl or optionally substituted heteroaryl, R c is hydrogen, and the other six of Ar 11 ~Ar 18 are each hydrogen.

[0120] As a preferable range of the anthracene-based compound represented by the formula (1), an anthracene-based compound represented by the following formula (1A), formula (1B), formula (1C), formula (1D), or formula (1E) can also be defined.

Chemical formula

[0121] In the formula (1A), formula (1B), formula (1C), formula (1D) and formula (1E), Ar c ’, Ar 11 ’, Ar 12 ’, Ar 13 ’, Ar 14 ’, Ar 15 ’, Ar 17 ’, and Ar 18's are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the following formula (A), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the following formula (A). Here, when all the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 's unbonded anthracene ring carbon atoms may have methyl or t-butyl bonded in place of hydrogen.

[0122] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 's are each preferably a group represented by any of the above formulas (1-X1) to (1-X7) when they are each substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl.

[0123] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18' is each independently phenyl, biphenylyl (especially, biphenyl-2-yl or biphenyl-4-yl), terphenylyl (especially, m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or a group represented by any of the following formulas (A-1) to (A-4). At this time, at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of the following formulas (A-1) to (A-4).

[0124] Further, at least one hydrogen in the compound represented by formula (1A), (1B), (1C), (1D), or (1E) may be substituted with halogen, cyano, or deuterium.

[0125] Hereinafter, the group represented by the above formula (A) will be described.

Chemical formula

[0126] In formula (A), Y is -O-, -S-, or >N-R 39 is. R 39 is hydrogen or optionally substituted aryl. Further, in formula (A), R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and R 21 ~R 28Of these, 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 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, alkyldicycloalkylsilyl, amino which may be substituted, halogen, hydroxy, or cyano. The group represented by formula (A) is a group obtained by removing one hydrogen at any position of formula (A), and * indicates that position.

[0127] R in formula (A) 21 ~R 28 Among them, it is preferable that all are hydrogen, or at least one is aryl which may be substituted or heteroaryl which may be substituted. It is more preferable that all are hydrogen, or at least one is aryl which may be substituted or heteroaryl which may be substituted and the others are hydrogen. It is even more preferable that all are hydrogen, or one or two of them are aryl which may be substituted or heteroaryl which may be substituted and the others are hydrogen. R 21 ~R 28 When adjacent groups among them are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, the hydrogen in the formed ring is not substituted with a substituent, and the remaining R 21 ~R 28 is hydrogen, or the substituent that substitutes the hydrogen in the formed ring and the remaining R 21 ~R 28 It is preferable that at least one of them is aryl which may be substituted or heteroaryl which may be substituted. The hydrogen in the formed ring is not substituted with a substituent, and the remaining R 21 ~R28 is hydrogen, or a substituent that replaces hydrogen in the formed ring and the remaining R 21 ~R 28 One or two of which are more preferably aryl which may be substituted or heteroaryl which may be substituted.

[0128] R in formula (A) 21 ~R 28 For the "alkyl" in the "optionally substituted alkyl", it may be either linear or branched. For example, linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms can be mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0129] Specific examples of the "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0130] R in formula (A) 21 ~R 28Examples of the "aryl" in the "optionally substituted aryl" 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.

[0131] Specific examples of the "aryl" include phenyl which is a monocyclic group, biphenylyl which is a bicyclic group, naphthyl which is a condensed bicyclic group, terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl) which is a tricyclic group, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl which are condensed tricyclic groups, triphenylenyl, pyrenyl, naphthacenyl, benzofluorenyl which are condensed tetracyclic groups, perylenyl, pentacenyl which are condensed pentacyclic groups, and the like.

[0132] R in formula (A) 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, still more preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Examples of the heteroaryl also include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0133] Specific "heteroaryl" includes, for example, 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, cinnolyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuranyl, naphthobenzothienyl, etc.

[0134] R in formula (A) 21 ~R 28 The "alkoxy" in the "optionally substituted alkoxy" in R

[0135] Specific "alkoxy" includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s - butoxy, t - butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, etc.

[0136] R in formula (A) 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is the group described as R 21 ~R 28 as described for "aryl" above.

[0137] R in formula (A) 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is substituted with an aryl, and this aryl is the group described as R 21 ~R 28 as described for "aryl" above.

[0138] R in formula (A) 21 ~R 28 The "trialkylsilyl" in R to R in formula (A) is a group in which the three hydrogens in silyl are each independently substituted with an alkyl, and this alkyl is the group described as R 21 ~R 28 as described for "alkyl" above. Preferred alkyls for substitution are alkyls having 1 to 4 carbon atoms, specifically methyl, ethyl, propyl, i-propyl, n-butyl, s-butyl, t-butyl, cyclobutyl, etc.

[0139] Specific examples of the "trialkylsilyl" group include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, s-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, s-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and the like.

[0140] R in formula (A) 21 ~R 28 Examples of the "substituted amino" of the "optionally substituted amino" in R 21 ~R 28 include amino groups in which two hydrogens are substituted with aryl or heteroaryl. An amino group in which two hydrogens are substituted with aryl is a diaryl-substituted amino, an amino group in which two hydrogens are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino group in which two hydrogens are substituted with aryl and heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl can be the groups described as "aryl" and "heteroaryl" in R

[0141] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0142] R in formula (A) 21 ~R 28 Examples of the "halogen" in R

[0143] R in formula (A) 21 ~R 28 Among the groups described as such, some may be substituted as described above, and examples of the substituent in this case include alkyl, aryl, or heteroaryl. This alkyl, aryl, or heteroaryl may be the group described as "alkyl", "aryl", or "heteroaryl" in the above-mentioned R 21 ~R 28 and can cite the groups described as "alkyl", "aryl", or "heteroaryl" in R

[0144] " >N-R 39 " as Y in formula (A), the R 39 is hydrogen or aryl which may be substituted, and as this aryl, the group described as "aryl" in the above-mentioned R 21 ~R 28 can be cited, and as its substituent, the groups described as substituents for R 21 ~R 28 can be cited.

[0145] R in formula (A) 21 ~R 28 Among them, 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 the group represented by the following formula (A-1), and examples of the case where a ring is formed include the groups represented by the following formulas (A-2) to (A-14). In addition, at least one hydrogen in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano, and these can cite the groups described as each group in the above-mentioned R 21 ~R 28 and can cite the groups described as each group in R

[0146] Examples of the ring formed by the adjacent groups bonding to each other include a cyclohexane ring in the case of a hydrocarbon ring, and the ring structures described above for "aryl" and "heteroaryl" in R 21 ~R 28 in the case of an aryl ring or a heteroaryl ring. These rings are formed so as to be condensed with one or two benzene rings in formula (A-1).

[0147] Examples of the group represented by formula (A) include groups represented by any of the following formulas (A-1) to (A-14). Among them, groups represented by any of formulas (A-1) to (A-11) are preferred, groups represented by any of formulas (A-1) to (A-4) are more preferred, groups represented by any of formula (A-1), formula (A-3) and formula (A-4) are even more preferred, and the group represented by formula (A-1) is most preferred.

[0148]

Chemical formula

[0149] The group represented by formula (A) is a group obtained by removing one hydrogen at any position in formula (A), and * indicates that position. That is, the group represented by formula (A) may have any position as the bonding position. Among them, any carbon atom on two benzene rings in the structure of formula (A), any atom on any ring formed by the adjacent groups among R 21 ~R 28 bonding to each other, or a group directly bonding to (having a bond to) N in ">N-R 39 " as Y in the structure of formula (A) is preferred.

[0150] Y in formula (A) and Y in each of formulas (A-1) to (A-14) are preferably -O-.

[0151] Examples of the group represented by formula (A) include groups represented by the following formulas. Y and * in the formulas have the same definitions as above, and Y is preferably -O-. [Chemical]

[0152] Compounds containing a group represented by formula (A) (especially a group represented by formula (A) where Y is -O-) are preferred examples of anthracene compounds represented by formula (1). In addition to the compounds already described, the following anthracene compounds of (a) or (b) are also preferred.

[0153] (a) In formula (1), Ar 14 , Ar 15 is optionally substituted aryl or optionally substituted heteroaryl, Ar 11 , Ar 12 , Ar 13 , Ar 16 , Ar 17 and Ar 18 are all hydrogen, and at least one selected from the group consisting of Ar C , Ar 14 and Ar 15 is a group represented by formula (A), and when R 21 ~R 28 and Y in formula (A) are >N-R 39 , at least one selected from the group consisting of R 39 is aryl or heteroaryl. An anthracene compound. R c is preferably hydrogen.

[0154] Specific examples include the 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).

[0155] (b) In formula (1), Ar 14 and Ar 15 are each independently an aryl which may be substituted or a heteroaryl which may be substituted. Ar 11 , Ar 12 , Ar 13 , Ar 16 , Ar 17 and Ar 18 are all hydrogen, and at least one selected from the group consisting of Ar C , Ar 14 and Ar 15 is an aryl having as a substituent a group represented by formula (A) or a heteroaryl having as a substituent a group represented by formula (A). Anthracene compound. R c is preferably hydrogen. Examples of the aryl having as a substituent a group represented by formula (A) include groups represented by any of formulas (1-X1) to (1-X6), wherein Ar 21 , Ar 22 , Ar 23 , Ar 24 , Ar 25 , or Ar 26 is a group represented by formula (A).

[0156] Specific examples include compounds represented by the following formula numbers in Table 1: (1-2912), (1-3284), (1-3736), (1-3770), (1-2873), (1-3249), (1-3296), (1-2917), (1-3768), (1-3780), (1-3963), (1-4112), (1-4052), (1-4047), (1-3778), (1-4168), (1-4510).

[0157] Hereinafter, the group represented by the aforementioned formula (B), the group represented by formula (C), the group represented by formula (D), and the group represented by formula (E) will be described. The description of each of the following substituents can refer to the description of R 21 to R 28 in formula (A).

[0158] [Chemical formula]

[0159] In formula (B), Y is -O-, -S- or >N-R 39 wherein. R 39 is hydrogen or an optionally substituted aryl. Also, in formula (B), R 29 ~R 38 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and adjacent groups among R 29 ~R 38 may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, 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 * indicates that position.

[0160] In formula (B), Y is preferably -O-. R in formula (B) 29 ~R 38Among them, it is preferable that all are hydrogen, or at least one is aryl which may be substituted or heteroaryl which may be substituted. Among them, it is more preferable that all are hydrogen, or at least one is aryl which may be substituted or heteroaryl which may be substituted, and the others are hydrogen. Among them, it is still more preferable that all are hydrogen, or one or two of them are aryl which may be substituted or heteroaryl which may be substituted, and the others are hydrogen. R 29 ~R 38 When adjacent groups among them are bonded to each other to form a hydrocarbon ring, aryl ring or heteroaryl ring, the hydrogen in the formed ring is not substituted with a substituent, and the remaining R 29 ~R 38 is hydrogen, or a substituent that substitutes hydrogen in the formed ring and the remaining R 29 ~R 38 of at least one is preferably aryl which may be substituted or heteroaryl which may be substituted. The hydrogen in the formed ring is not substituted with a substituent, and the remaining R 29 ~R 38 is hydrogen, or one or two of a substituent that substitutes hydrogen in the formed ring and the remaining R 29 ~R 38 are preferably aryl which may be substituted or heteroaryl which may be substituted.

[0161] Examples of the group represented by formula (B) include, for example, the group represented by the following formula (B-1).

[0162]

Chemical formula

[0163] As the group represented by formula (B), more specifically, the groups represented by the following formulas are given as examples. Y and * in the formulas have the same definitions as above, and Y is preferably -O-.

[0164] [Chemical formula]

[0165] In formula (C), Y is -O-, -S-, or >N-R 39 wherein R 39 is hydrogen or aryl which may be substituted. Further, in formula (C), R 41 ~R 48 are each 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, alkyldicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, and adjacent groups among R 41 ~R 48 may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with 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, alkyldicycloalkylsilyl, amino which may be substituted, halogen, hydroxy, or cyano.

[0166] The group represented by formula (C) is a group obtained by removing one hydrogen at any position of formula (C), and * indicates that position. In formula (C), when Y is >N-R 39 wherein R 39 is preferably phenyl which may be substituted, more preferably unsubstituted phenyl. R 39The phenyl which may be substituted is R 42 , R 43 , R 46 , or R 47 may be bonded to the benzene ring as a bonding hand. It is preferable that at least one of Y is -O-, and all of Y are -O-, or one of Y is -O- and the other is >N-R 39 is more preferable. It is preferable that all of R 41 ~R 48 are hydrogen.

[0167] Examples of the group represented by formula (C) include a group represented by the following formula (C-1).

[0168]

Chemical formula

[0169] As the group represented by formula (C), more specifically, a group represented by the following formula can be given as an example. Y and * in the formula have the same definitions as above, and it is preferable that Y is -O-.

[0170]

Chemical formula

[0171] In formula (D), Y is -O-, -S-, or >N-R 39 . R 39 is hydrogen or an aryl which may be substituted. Also, in formula (D), R 51 ~R 58 are each independently hydrogen, an alkyl which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, a heteroaryl which may be substituted, an alkoxy which may be substituted, an aryloxy which may be substituted, an arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, an amino which may be substituted, halogen, hydroxy or cyano, and R51 ~R 58 Among them, 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 optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxy, or a cyano.

[0172] The group represented by formula (D) is a group obtained by removing one hydrogen at any position of formula (D), and * indicates that position. In formula (D), Y is preferably -O-. R 51 ~R 58 are all preferably hydrogen.

[0173] In formula (E), Y is -O-, -S-, or >N-R 39 is. R 39 is hydrogen or an optionally substituted aryl. Further, in formula (E), R 61 ~R 71 are each independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxy or a cyano, and R 61 ~R 71Among them, 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 which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, a heteroaryl which may be substituted, an alkoxy which may be substituted, an aryloxy which may be substituted, an arylthio which may be substituted, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an amino which may be substituted, a halogen, a hydroxy, or a cyano.

[0174] The group represented by formula (E) is a group obtained by removing one hydrogen at any position of formula (E), and * indicates that position. In formula (E), when Y is >N-R 39 When it is, R 39 Is preferably a phenyl which may be substituted, and more preferably an unsubstituted phenyl. R 39 The optionally substituted phenyl where R 61 Is R 62 Is R 69 Or R 70 May be bonded to the benzene ring as a bond. Y is preferably at least one is -O-, and more preferably all are -O-. R 61 ~R 71 Is preferably hydrogen, phenyl, biphenyl, or naphthyl, and more preferably all are hydrogen.

[0175] As a particularly preferred anthracene compound represented by formula (1), an anthracene compound represented by the following formula (1Aa) can be mentioned.

Chemical formula

[0176] In formula (1Aa), Ar c ’, Ar 14’, and Ar 15 ’ is each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of the above formulas (A-1) to (A-11), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-11). Here, when all of the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Also, Ar c ’, Ar 14 ’, and Ar 15 ’ may be substituted with methyl or t-butyl instead of hydrogen at the carbon atom on the anthracene ring to which they are not bonded. 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) is substituted with deuterium.

[0177] In formula (1Aa), Ar c ’, Ar 14 ’, and Ar 15 ’ are each independently preferably phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of the above formulas (A-1) to (A-4), and at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of formulas (A-1) to (A-4).

[0178] In the compound represented by formula (1Aa), at least, the carbon at the 10-position of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon to which ’ is bonded (taking the carbon as the 9-position) is replaced with deuterium. That is, the compound represented by the formula (1Aa) is preferably a compound represented by the following formula (1Ab). In the formula (1Ab), D is deuterium, and Ar c ’, Ar 14 ’, and Ar 15 ’ are the same as the definitions in the formula (1Aa). D in the formula (1Ab) indicates that at least this position is deuterium, and one or more of the other hydrogens in the formula (1Aa) may be deuterium at the same time, and it is also preferable that all the hydrogens in the formula (1Aa) are deuterium.

[0179]

Chemical formula

[0180] Compounds represented by the formulas (1-1) to (1-5179), which are specific examples of the compound represented by the formula (1), are shown in Table 1 below. However, the present invention is not limited by the disclosure of these specific structures. In Table 1, D is deuterium, Me is methyl, tBu is t-butyl, CyHex is cyclohexyl, and other symbols will be described later.

[0181]

Table 1

[0182] The substituents represented by the symbols used in Table 1 are shown below. When the symbol in the structural formula of the substituents shown below has Y as O and is described in Table 1, it represents a substituent in which -Y- in the structural formula is -O- (for example, HCO-1). When the symbol with Y as S is described in Table 1, it represents a substituent in which -Y- in the structural formula is -S- (for example, HCS-1). When the symbol with Y as N is described in Table 1, it represents a substituent in which -Y- in the structural formula is >N-Ph (Ph is phenyl) (for example, HCN-1). Also, when the symbol with Z as O in the structural formula of the substituents shown below is described in Table 1, it represents a substituent in which -Z- in the structural formula is -O- (for example, DHCO-1). When the symbol with Z as S is described in Table 1, it represents a substituent in which -Z- in the structural formula is -S- (for example, DHCS-1). When the symbol with Z as N is described in Table 1, it represents a substituent in which -Z- in the structural formula is >N-C 6 D 5 represents a substituent that is (for example, DHCN-1). Also, in the following structural formulas, D is deuterium, Me is methyl, tBu is t-butyl, and * indicates the bonding position.

[0183] [Chemical formula]

[0184] [Chemical formula]

[0185] [Chemical formula]

[0186] [Chemical formula]

[0187] [Chemical formula]

[0188] [Chemical]

[0189] [Chemical]

[0190] [Chemical]

[0191] [Chemical]

[0192] [Chemical]

[0193] [Chemical]

[0194] [Chemical]

[0195] [Chemical]

[0196] [Chemical]

[0197] [Chemical]

[0198] [Chemical]

[0199]

Chem.

[0200]

Chem.

[0201]

Chem.

[0202]

Chem.

[0203]

Chem.

[0204]

Chem.

[0205]

Chem.

[0206]

Chem.

[0207]

Chem.

[0208]

Chem.

[0209] [Chemical]

[0210] [Chemical]

[0211] [Chemical]

[0212] [Chemical]

[0213] [Chemical]

[0214] [Chemical]

[0215] [Chemical]

[0216] [Chemical]

[0217] [Chemical]

[0218] [Chemical]

[0219] [Chemical]

[0220]

Chem.

[0221]

Chem.

[0222]

Chem.

[0223]

Chem.

[0224]

Chem.

[0225]

Chem.

[0226]

Chem.

[0227] Among the above compounds, the compound represented by the following formula is preferred. In the following formula, D represents deuterium, Me represents methyl, tBu represents t-butyl, and CyHex represents cyclohexyl.

Chem.

[0228]

Chem.

[0229]

Chem.

[0230]

Chem.

[0231]

Chem.

[0232]

Chem.

[0233]

Chem.

[0234]

Chem.

[0235]

Chem.

[0236]

Chem.

[0237]

Chem.

[0238]

Chem.

[0239]

Chem.

[0240] [Chemistry]

[0241] [Chemistry]

[0242] [Chemistry]

[0243] [Chemistry]

[0244] [Chemistry]

[0245] [Chemistry]

[0246] [Chemistry]

[0247] [Chemistry]

[0248] [Chemistry]

[0249] [Chemistry]

[0250] [Chemistry]

[0251]

Chem.

[0252]

Chem.

[0253]

Chem.

[0254]

Chem.

[0255]

Chem.

[0256]

Chem.

[0257] 1-1-2. Method for producing an anthracene-based compound The anthracene-based compound represented by formula (1) can be produced by a method according to the production methods described in International Publication No. WO2006 / 003842, Korean Patent Publication No. KR2017-116885, International Publication No. WO2009 / 142230, etc.

[0258] 1-2-1. Polycyclic aromatic compound represented by formula (2) and its multimer The organic EL element of the present invention contains, as a dopant material in the light-emitting layer, a polycyclic aromatic compound represented by the following formula (2) and a multimer of a polycyclic aromatic compound having a plurality of structures represented by the formula (2). 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 multimer 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).

[0259]

Chemical formula

[0260] In each structural formula, "A" to "C" and "a" to "c" are symbols indicating ring structures represented by a ring, a benzene ring, or a 5-membered ring, respectively, and the other symbols are the same as the definitions described above.

[0261] The A ring, B ring, and C ring in the formula (2) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. This substituent is preferably 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 (an amino having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (the two aryls 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, or a substituted silyl. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0262] 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 with a substituent.

[0263] It is preferable that at least one of ring A, ring B, and ring C is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent. More preferably, each of ring A, ring B, and ring C is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent. Even more preferably, each of ring A, ring B, and ring C is an aryl ring having one substituent or a heteroaryl ring having one substituent.

[0264] Examples of the substituent at this time include substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl.

[0265] Particularly, as the substituent, substituted or unsubstituted alkyl (particularly, neopentyl) and cycloalkyl such as adamantyl are preferable. Also, tertiary-alkyl (tR) is preferable. This is because such bulky substituents prevent deactivation due to aggregation of molecules and improve the photoluminescence quantum yield (PLQY). Also, substituted or unsubstituted diarylamino is also preferable as the substituent.

[0266] The tertiary-alkyl is represented by the following formula (tR). [Chemical formula]

[0267] In formula (tR), R a , R b , and R c are each independently an alkyl group having 1 to 24 carbon atoms, and any -CH 2 - in the alkyl group may be replaced by -O-, and the group represented by formula (tR) substitutes at least one hydrogen in the compound or structure represented by formula (2) at *.

[0268] R a , R b , and R c The "alkyl group having 1 to 24 carbon atoms" for R

[0269] , R a , and R b in formula (tR) of formula (2) may be either a straight-chain or a branched-chain, and examples include a straight-chain alkyl group having 1 to 24 carbon atoms or a branched-chain alkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (a branched-chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched-chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched-chain alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (a branched-chain alkyl group having 3 to 4 carbon atoms). c The total number of carbon atoms of R

[0270] , R a , and R b in formula (tR) of formula (2) is preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms. cSpecific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

[0271] Examples of the group represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl group, and the like. Among these, t-butyl and t-amyl are preferred.

[0272] Other preferred examples of the substituents in Ring A, Ring B, and Ring C include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), or benzocarbazolyl substituted with a group of formula (tR). Examples of the group described as the following "first substituent" for "diarylamino" can be given. As the substitution form of the group of formula (tR) for diarylamino, carbazolyl, and benzocarbazolyl, examples 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).

[0273] The aryl ring or heteroaryl ring in Ring A, Ring B, and Ring C preferably has a 5-membered ring or 6-membered ring that shares a bond with the central fused 2-ring structure of formula (2) composed of "B", "X 1 ", and "X 2 ".

[0274] Here, the "fused 2-ring structure" means a structure in which two saturated hydrocarbon rings composed of "B", "X 1 ", and "X 2 " shown in the center of formula (2) are fused. The "6-membered ring that shares a bond with the fused 2-ring structure" means, for example, the a-ring (benzene ring (6-membered ring)) fused to the said fused 2-ring structure as shown in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). Also, "(the aryl ring or heteroaryl ring which is Ring A) has this 6-membered ring" means that Ring A is formed only by this 6-membered ring, or Ring A is formed by further fusing other rings or the like to this 6-membered ring so as to include this 6-membered ring. In other words, the "aryl ring or heteroaryl ring (which is Ring A) having a 6-membered ring" referred to here means that the 6-membered ring constituting all or part of Ring A is fused to the said fused 2-ring structure. The same explanation applies to the "5-membered ring". The same explanation also applies to "Ring B (b-ring)" and "Ring C (c-ring)".

[0275] The A ring in formula (2) corresponds to the a ring and its substituents R in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 1 ~R 3 The B ring in formula (2) corresponds to the b ring and its substituents R in formula (2-a), formula (2-b), and formula (2-c), 8 ~R 11 the b ring and its substituents R in formula (2-d), 10 and R 11 as well as the b ring and its substituents R in formula (2-e) and formula (2-f). 8 and R 9 The C ring in formula (2) corresponds to the c ring and its substituents R in formula (2-a), 4 ~R 7 the c ring and its substituents R in formula (2-b), formula (2-d), and formula (2-f), 4 and R 5 as well as the c ring and its substituents R in formula (2-c) and formula (2-e). 6 and R 7 That is, formula (2-a) corresponds to a structure in which at least a 6-membered ring structure is selected as the A to C rings of formula (2), and formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) each correspond to a structure in which at least a 6-membered ring structure and at least a 5-membered ring structure are selected as the A to C rings of formula (2). In that sense, each ring in formula (2-a) etc. is represented by lowercase a to c.

[0276] X in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) X is independently >O, >S, >N-R, or >C(-R) 2 wherein R in >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, preferably optionally substituted aryl, more preferably unsubstituted aryl. Also, >C(-R) 2Each R is independently aryl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, preferably alkyl, more preferably methyl. >C(-R) 2 The two Rs in 2 are preferably the same. Also >C(-R) 2 The two Rs in 2 preferably form a ring with each other. X X is independently preferably >O, >S, or >N-R, more preferably >O or >S, even more preferably >S.

[0277] In formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0278] R 1 ~R 11 are each independently preferably hydrogen, alkyl (especially the above-mentioned tertiary-alkyl (tR), neopentyl, etc.), cycloalkyl (such as adamantyl, etc.), substituted or unsubstituted diarylamino, or substituted silyl (triphenylsilyl, trimethylsilyl, etc.).

[0279] In each of formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), R 1 ~R 3Among them, 0 to 1 is other than hydrogen (the above-mentioned preferred substituent of the special), and the others are hydrogen, R 4 ~R 7 Among them, 0 to 1 is other than hydrogen (the above-mentioned preferred substituent of the special), and the others are hydrogen, R 8 ~R 11 Among them, it is preferable that 0 to 1 is other than hydrogen (the above-mentioned preferred substituent of the special), and the others are hydrogen, R 1 ~R 3 Among them, 1 is other than hydrogen (the above-mentioned preferred substituent of the special), and the others are hydrogen, R 4 ~R 7 Among them, 1 is other than hydrogen (the above-mentioned preferred substituent of the special), and the others are hydrogen, R 8 ~R 11 Among them, it is more preferable that 1 is other than hydrogen (the above-mentioned preferred substituent of the special), and the others are hydrogen.

[0280] In formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), the substituents R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 and R 11 Among them, adjacent groups may combine with each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0281] For example, depending on the mutual bonding forms of the substituents in the a-ring, b-ring, and c-ring, the ring structure constituting the compound changes as shown in the following formulas (2-a-1) and (2-a-2). The A'-ring, B'-ring, and C'-ring in each formula correspond to the A-ring, B-ring, and C-ring in formula (2), respectively. Also, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 and R 11 、a, b, c, X 1 and X 2 are defined in the same way as in formula (2-a).

[0282]

Chemical formula

[0283] The A'-ring, B'-ring, and C'-ring in formulas (2-a-1) and (2-a-2), when explained by formula (2-a), mean that adjacent groups among the substituents R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、and R 11 are bonded to each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring, and c-ring respectively (it can also be said to be a condensed ring formed by condensing another ring structure to the a-ring, b-ring, or c-ring). Although not shown in the formula, there is also a compound in which all of the a-ring, b-ring, and c-ring have changed to the A'-ring, B'-ring, and C'-ring. Also, as can be seen from formulas (2-a-1) and (2-a-2), for example, R 8 of the b-ring and R 7 of the c-ring, R 11 of the b-ring and R 1 of the a-ring, R 4and R of the a-ring 3 Groups such as these do not fall under "adjacent groups", and they do not combine. That is, "adjacent groups" means groups adjacent on the same ring.

[0284] Compounds represented by formula (2-a-1) or formula (2-a-2) correspond to, for example, compounds represented by formula (2-67) to formula (2-74), formula (2-76) to formula (2-83), formula (2-273) to formula (2-276), formula (2-290) to formula (2-295), and formula (2-350) to formula (2-355) listed as specific compounds described later. That is, for example, a benzene ring which is the a-ring (or b-ring or c-ring) in formula (2-a), 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 is condensed to form a compound having an A'-ring (or B'-ring or C'-ring), and the formed condensed ring A' (or condensed ring B' or condensed ring C') is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring, or a fluorene ring, respectively.

[0285] Also, in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), similarly, a condensed ring formed by condensing another ring structure to the a-ring, b-ring, or c-ring may be formed. For example, a benzene ring which is the a-ring or b-ring may form a condensed ring by condensing another ring structure in the same manner as the benzene ring in the above formula (1-a).

[0286] In formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), in the 5-membered ring which is the b-ring or c-ring, R 4 ~R 11 It is particularly preferable that adjacent groups among them combine to form a ring and a condensed ring is formed. For example, in the c-ring of formula (2-b) and formula (2-c), and the b-ring and c-ring of formula (2-d), formula (2-e), and formula (2-f), R 3 ~R 11Among them, adjacent groups can combine with each other to form a ring, thereby forming a condensed ring B' ring or C' ring. Examples of the condensed ring when the formed ring is a benzene ring include an indole ring, a benzofuran ring, and a benzothiophene ring. Examples of such structures include compounds represented by any of the following formulas (2-572) to (1-588).

[0287] For example, in formulas (2-b), (2-c), (2-d), (2-e), and (2-f), for example, when X X is >O, the b ring or c ring becomes a furan ring, and the ring corresponding to the B' ring or C' ring of formula (2-a-1) formed by condensing a benzene ring with this furan ring is a benzofuran ring. Also, for example, in formulas (2-b), (2-c), (2-d), (2-e), and (2-f), for example, when X X is >S, the b ring or c ring becomes a thiophene ring, and the ring corresponding to the B' ring or C' ring of formula (2-a-1) formed by condensing a benzene ring with this thiophene ring is a benzothiophene ring.

[0288] As an example, in the 5-membered ring which is the c ring of formula (2-b), an example where R 4 and R 5 combine with each other to form a benzene ring and a condensed ring is shown below.

Chemical Structure

[0289] In formula (2-b-1), R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , X X , Y 1 , X 1 and X 2 are synonymous with those in formula (2-b), and the preferred ranges are also the same. R 4b , R 5b, R 6b , R 7b is a substituent selected from the group consisting of hydrogen, or aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. R 4b , R 5b , R 6b , R 7b Among them, it is preferable that 0 to 2 are substituents other than hydrogen and the others are hydrogen, and it is more preferable that 1 is a substituent other than hydrogen and the others are hydrogen. As the substituent other than hydrogen, the preferable range can refer to the description of the substituents described later as the first substituent (which may have a second substituent). As the substituent other than hydrogen, alkyl (especially the above-mentioned tertiary-alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino is particularly preferable.

[0290] X in formula (2) 1 and X 2 are each independently >O, >N-R, >C(-R) 2 , >S, or >Se, and R in the >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in the >C(-R) 2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in the >N-R and / or R in the >C(-R) 2 may be bonded to the B ring and / or C ring via a linking group or a single bond, and as the linking group, -O-, -S-, or -C(-R) 2 - is preferable. Note that the "-C(-R) 2The "R" in "-" is hydrogen, alkyl, or cycloalkyl. This description applies to X in Formula (2-a), Formula (2-b), Formula (2-c), Formula (2-d), Formula (2-e), and Formula (2-f). 1 and X 2 are the same too.

[0291] In Formula (2), Formula (2-a), Formula (2-b), Formula (2-c), Formula (2-d), Formula (2-e), and Formula (2-f), X 1 and X 2 are each independently preferably >O or >N-R, more preferably >N-R where R is optionally substituted phenyl, even more preferably >N-R where at least one R is phenyl substituted with one or two t-butyl, t-amyl, methyl or phenyl, and particularly preferably >N-R where at least one R is phenyl substituted with one t-butyl or t-amyl. X 1 and X 2 may be the same or different from each other.

[0292] Here, the provision that "the R of >N-R and / or >C(-R) in Formula (2) is bonded to the A ring, B ring, and / or C ring by a linking group or a single bond" corresponds to the provision that "the R of >N-R and / or >C(-R) in Formula (2-a), Formula (2-b), Formula (2-c), Formula (2-d), Formula (2-e), and Formula (2-f) is bonded to the a ring, b ring, and / or c ring by -O-, -S-, -C(-R) 2 - or a single bond". 2 This provision can be expressed by a compound having a ring structure in which X 2 and X

[0293] are incorporated into the condensed ring B' and the condensed ring C', as represented by the following Formula (2-a-3-1). That is, for example, for the benzene ring which is the b ring (or c ring) in Formula (2-a), X 1 or X 2 is incorporated into the condensed ring B' and the condensed ring C'. That is, for example, for the benzene ring which is the b ring (or c ring) in Formula (2-a), X 1 (or X 2It is a compound having a B' ring (or C' ring) formed by the condensation of other rings so as to incorporate . The formed condensed ring B' (or condensed ring C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0294] Further, the above provisions can also be expressed as a compound having a ring structure in which X 1 and / or X 2 is incorporated into the condensed ring A'. That is, for example, with respect to the benzene ring which is the a ring in formula (2-a), X 1 (and / or X 2 ) is a compound having an A' ring formed by the condensation of other rings so as to incorporate. The formed condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0295]

Chemical formula

[0296] Examples of the "aryl ring" which is the A ring, B ring, and C ring in formula (2) 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. Note that this "aryl ring" corresponds to the benzene ring in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), and the "aryl ring" formed by the bonding of adjacent groups among "R 1 ~R 11 together with the a ring, b ring, or c ring.

[0297] Specific "aryl rings" include a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring which is a condensed bicyclic system, a tetralin ring, a terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) which is a tricyclic system, an anthracene ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring which are condensed tricyclic systems, a triphenylene ring, a pyrene ring, a naphthacene ring which are condensed tetracyclic systems, a perylene ring, a pentacene ring which are condensed pentacyclic systems, and the like.

[0298] Examples of the "heteroaryl ring" which is 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. Further, examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms. Note that this "heteroaryl ring" corresponds to a 5-membered ring in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), and a heteroaryl ring formed by the bonding of adjacent groups among "R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、and R 11 together with the a ring, b ring, or c ring.

[0299] Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, phthalazan ring, oxadiazole ring, thianthrene ring, and the like.

[0300] In the above, the "aryl rings" and "heteroaryl rings" of Ring A, Ring B, and Ring C may share a bond with the central fused bicyclic structure of Formula (2) at any position. For example, when the "aryl ring" and "heteroaryl ring" are fused rings in which two or more rings are fused, any ring may share a bond with the central fused bicyclic structure of Formula (1). Among these, as described above, Ring A, Ring B, and Ring C preferably have a 5-membered or 6-membered ring that shares a bond with the central fused bicyclic structure of Formula (2) composed of B, X 1 , and X 2 . That is, for example, in Formula (2-a), when adjacent groups among R 1 to R 3 , R 4 to R 7 , and R 8 to R 11 are bonded to each other to form an aryl ring or heteroaryl ring together with Ring a, Ring b, or Ring c (a benzene ring which is a 6-membered ring shares a bond with the central fused bicyclic structure of Formula (2)), and in Formula (2-b), (2-c), Formula (2-d), Formula (2-e), or Formula (2-f), R 4 to R11 When adjacent groups among them are bonded to form an aryl ring or a heteroaryl ring together with the b-ring and the c-ring (a 5-membered ring shares a bond with the central condensed 2-ring structure of the formula (2)), it is preferable. Examples of the 5-membered ring at this time include a pyrrole ring, a furan ring, and a thiophene ring.

[0301] At least one hydrogen in the above-mentioned "aryl ring" or "heteroaryl ring" is a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diaryl amino", a substituted or unsubstituted "diheteroaryl amino", a substituted or unsubstituted "aryl heteroaryl amino", a substituted or unsubstituted "diaryl boryl (two aryls 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 may be substituted with a substituted silyl. However, as the first substituent, the "aryl", "heteroaryl", the aryl of "diaryl amino", the heteroaryl of "diheteroaryl amino", the aryl and heteroaryl of "aryl heteroaryl amino", the aryl of "diaryl boryl", and the aryl of "aryloxy" are the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring".

[0302] Also, as the "alkyl" as the first substituent, it may be either linear or branched. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. An alkyl having 1 to 18 carbon atoms (a branched alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (a branched alkyl having 3 to 12 carbon atoms) is more preferable, an alkyl having 1 to 6 carbon atoms (a branched alkyl having 3 to 6 carbon atoms) is still more preferable, and an alkyl having 1 to 5 carbon atoms (a branched alkyl having 3 to 5 carbon atoms) is particularly preferable.

[0303] Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

[0304] Examples of the "cycloalkyl" as the first substituent include cycloalkyls having 3 to 24 carbon atoms, preferably cycloalkyls having 3 to 20 carbon atoms, more preferably cycloalkyls having 3 to 16 carbon atoms, still more preferably cycloalkyls having 3 to 14 carbon atoms, still more preferably cycloalkyls having 5 to 10 carbon atoms, particularly preferably cycloalkyls having 5 to 8 carbon atoms, and most preferably cycloalkyls having 5 to 6 carbon atoms.

[0305] Specific cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their C1-C4 alkyl (especially methyl) substituents, 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, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0306] Examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0307] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0308] Examples of the "substituted silyl" as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. For example, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl can be mentioned.

[0309] Examples of the "trialkylsilyl" include groups in which three hydrogens in silyl are each independently substituted with alkyl, and this alkyl can cite the groups described as the "alkyl" in the above-mentioned first substituent. Preferred alkyl for substitution is alkyl having 1 to 5 carbon atoms, and specifically, methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, t-amyl, and the like can be mentioned.

[0310] Specific trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyl dimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyl diethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyl dipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, t-amyl di-i-propylsilyl, etc.

[0311] "Tricycloalkylsilyl" includes groups in which the three hydrogens in silyl are each independently substituted with cycloalkyl, and this cycloalkyl can cite the groups described as "cycloalkyl" in the above-mentioned first substituent. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, etc.

[0312] Specific tricycloalkylsilyls include tricyclopentylsilyl, tricyclohexylsilyl, etc.

[0313] Specific examples of a dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and an alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyls substituted with groups selected from the specific alkyls and cycloalkyls described above.

[0314] Specific examples of a dialkylarylsilyl substituted with two alkyls and one aryl, an alkyldiarylsilyl substituted with one alkyl and two aryls, and a triarylsilyl substituted with three aryls include silyls substituted with groups selected from the specific alkyls and aryls described above. Specific examples of the triarylsilyl include, in particular, triphenylsilyl.

[0315] Also, as the "aryl" in "diarylboronyl" as the first substituent, the description of the aryl described above can be cited. Further, these two aryls may be bonded via a single bond or a linking group (for example, >C(-R) 2 , >O, >S or >N-R). Here, R in >C(-R) 2 and >N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl (the above, the first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl (the above, the second substituent). Specific examples of these groups can cite the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy as the first substituent described above.

[0316] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron-donating property, and electron-withdrawing property of the structure of the first substituent. Preferably, it is a group represented by the following structural formula. More preferably, it is methyl, t-butyl, t-pentyl (t-amyl), t-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy. Even more preferably, it is methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis. Specifically, t-butyl, t-pentyl (t-amyl), t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferable.

[0317] In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bonding position.

Chemical formula

[0318]

Chemical formula

[0319]

Chemical formula

[0320]

Chem.

[0321]

Chem.

[0322]

Chem.

[0323]

Chem.

[0324]

Chem.

[0325]

Chem.

[0326]

Chem.

[0327]

Chem.

[0328]

Chem.

[0329]

Chem.

[0330] 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 , it is preferable that 1 to 4 of them are groups represented by any of the above structural formulas and the rest are hydrogen. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 , it is more preferable that 1 to 3 of them are groups represented by any of the above structural formulas and the rest are hydrogen. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 , it is even more preferable that 1 to 3 of them are methyl, t-butyl or t-amyl and the rest are hydrogen.

[0331] The first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diaryl amino", a substituted or unsubstituted "diheteroaryl amino", a substituted or unsubstituted "aryl heteroaryl amino", a substituted or unsubstituted "diaryl boryl (the two aryls 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 described as substituted or unsubstituted, at least one hydrogen in them may be substituted with a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, and specific examples thereof can be referred to the monovalent groups of the "aryl ring" or "heteroaryl ring" described above, or the descriptions of "alkyl", "cycloalkyl", or substituted silyl as the first substituent. Further, for aryl and heteroaryl as the second substituent, structures in which at least one hydrogen in them is substituted with aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described above), or cycloalkyl such as cyclohexyl (specific examples are the groups described above) are also included in aryl and heteroaryl as the second substituent. As an example thereof, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen at the 9-position is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl is also included in heteroaryl as the second substituent.

[0332] R in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11As the aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboril, or aryl of aryloxy in [description], a monovalent group of the "aryl ring" or "heteroaryl ring" described in formula (2) can be mentioned. Also, R 1 ~R 11 As the alkyl, cycloalkyl or alkoxy in [description], reference can be made to the descriptions of "alkyl", "cycloalkyl" or "alkoxy" as the first substituent in the description of formula (2) above. Further, the same applies to aryl, heteroaryl, alkyl or cycloalkyl as substituents for these groups. Also, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、and R 11 When adjacent groups among them are bonded to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring, or c-ring, for the substituents on these rings, such as heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril, alkyl, cycloalkyl, alkoxy or aryloxy, and further substituents such as aryl, heteroaryl, alkyl, or cycloalkyl, the same applies.

[0333] X in formula (2) 1 and X 2In >N-R, R is aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in aryl or heteroaryl may be substituted with, for example, alkyl, cycloalkyl, or substituted silyl. Examples of this aryl, heteroaryl, alkyl, and cycloalkyl include the groups described above. Particularly preferred are aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This description applies to X in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 1 and X 2 are the same. X in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 1 and X 2 In >N-R, R is aryl having 6 to 12 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, heteroaryl having 2 to 15 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and is preferably aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms.

[0334] X of formula (2) 1 and X 2 In >C(-R) 2R is hydrogen, aryl, alkyl, or cycloalkyl, and at least one hydrogen in the aryl may be substituted with, for example, alkyl, cycloalkyl, or substituted silyl. Examples of this aryl, alkyl, and cycloalkyl include the groups described above. Particularly preferred are aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This description applies to X in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 1 and X 2 are the same. X in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 1 and X 2 In >C(-R) 2 R is aryl having 6 to 12 carbon atoms which may be substituted with hydrogen, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and is preferably aryl having 6 to 10 carbon atoms which may be substituted with hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms.

[0335] The R in the linking group “-C(-R) 2 -” in formula (2) is hydrogen, alkyl, or cycloalkyl, and examples of this alkyl and cycloalkyl include the groups described above. Particularly preferred are alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This description also applies to the linking group “-C(-R) 2 -” in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f).

[0336] The dopant material may be a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2). The multimer is preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the above unit structures in one compound. For example, in addition to a form in which the above unit structures are bonded by a plurality of linking groups such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group, any ring (ring A, ring B, or ring C, ring a, ring b, or ring c) contained in the above unit structure may be shared by a plurality of unit structures and bonded, or any rings (ring A, ring B, or ring C, ring a, ring b, or ring c) contained in the above unit structure may be condensed and bonded to each other.

[0337] 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). Each symbol in these formulas has the same meaning as that in formula (2-a), and the preferred ranges are also the same. The multimer compound represented by the following formula (2-4) is a multimer compound having a unit structure represented by a plurality of formula (2-a) in one compound such that the benzene ring which is the a ring is shared. Further, the multimer compound represented by the following formula (2-4-1) is a multimer compound having a unit structure represented by two formula (2-a) in one compound such that the benzene ring which is the a ring is shared. Further, the multimer compound represented by the following formula (2-4-2) is a multimer compound having a unit structure represented by three formula (2-a) in one compound such that the benzene ring which is the a ring is shared. Further, the multimer compounds represented by the following formula (2-5-1) to formula (2-5-4) are multimer compounds having a unit structure represented by a plurality of formula (2) in one compound such that the benzene ring which is the b ring (or c ring) is shared. Further, the multimer compound represented by the following formula (2-6) is a multimer compound having a unit structure represented by a plurality of formula (2-a) in one compound such that, for example, the benzene ring which is the b ring (or a ring, c ring) of a certain unit structure and the benzene ring which is the b ring (or a ring, c ring) of a certain unit structure are condensed.

[0338] [Chemical formula]

[0339] The multimer compound may be a multimer in which a multimeric form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) is combined with a multimeric form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6), or may be a multimer in which a multimeric form represented by any one of formulas (2-5-1) to (2-5-4) is combined with a multimeric form represented by formula (2-6), or may be a multimer in which a multimeric form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), a multimeric form represented by any one of formulas (2-5-1) to (2-5-4), and a multimeric form represented by formula (2-6) are combined.

[0340] In addition, all or part of the hydrogens in the chemical structures of the polycyclic aromatic compounds represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) and their multimers may be deuterium, cyano or halogen. For example, in formula (2), ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), substituents on rings A to C, and X 3 and X 4 when is >N-R or >C(-R) 2 the hydrogen in R (= alkyl, cycloalkyl, aryl) can be substituted with deuterium, cyano or halogen, and among these, there are embodiments in which all or part of the hydrogens in aryl or heteroaryl are substituted with deuterium, cyano or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

[0341] In addition, at least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structures of the polycyclic aromatic compounds represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) and their multimers may be condensed with at least one cycloalkane.

[0342] For example, aryl rings and heteroaryl rings among the A ring, B ring, C ring, a ring, b ring, and c ring, aryl (aryl moiety in aryl, diarylamino, arylheteroaryl amino, diarylboril, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroaryl amino, or arylheteroaryl amino) as the first and second substituents in the A ring to C ring, aryl (as above) and heteroaryl (as above) as the first and second substituents to the a ring, b ring, and c ring, and X 1 X 2 >N-R and >C(-R) 2 At least one of aryl (as above) and heteroaryl (as above) as R in >N-R and >C(-R) may be condensed with at least one cycloalkane.

[0343] Preferably, aryl rings and heteroaryl rings among the A ring, B ring, C ring, a ring, b ring, and c ring, aryl (aryl moiety in aryl, diarylamino, diarylboril, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroaryl amino) as the first substituent in the A ring to C ring, aryl (as above) and heteroaryl (as above) as the first substituent to the a ring, b ring, and c ring, and X 1 X 2 >N-R and >C(-R) 2 At least one of aryl (as above) and heteroaryl (as above) as R in >N-R and >C(-R) may be condensed with at least one cycloalkane.

[0344] More preferably, aryl rings among the A ring, B ring, C ring, a ring, b ring, and c ring, aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituent in the A ring to C ring, aryl (as above) and heteroaryl (as above) as the first substituent to the a ring, b ring, and c ring, and X 1 X2 >N-R and >C(-R) 2 At least one of the aryls (as defined above) as R of 2 may be fused with at least one cycloalkane.

[0345] More preferably, aryl rings such as ring A, ring B, ring C, ring a, ring b, and ring c, aryl as the first substituent in ring A to ring C (aryl moiety in aryl or diarylamino), aryl as the first substituent to ring a, ring b, and ring c (as defined above), and X 1 X 2 >N-R and >C(-R) 2 At least one of the aryls (as defined above) as R of 2 may be fused with at least one cycloalkane.

[0346] Examples of the "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0347] Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, 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, diamantane, decahydronaphthalene, and decahydroazulene, and their C1-C5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents, and deuterium substituents.

[0348] Among these, a structure in which at least one hydrogen at the α-position carbon of the cycloalkane (in the 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 preferred, a structure in which two hydrogens at the α-position carbon are substituted is more preferred, and a structure in which a total of four hydrogens at two α-position carbons are substituted is even more preferred. Examples of this substituent include an alkyl (especially methyl) substituent having 1 to 5 carbon atoms, a halogen (especially fluorine) substituent, and a deuterium substituent.

[0349] In particular, it is preferable that a partial structure represented by the following formula (B10) or formula (B11) is bonded to adjacent carbon atoms in the aryl ring or heteroaryl ring.

[0350]

Chemical formula

[0351] In formula (B10) and formula (B11), Me represents methyl. * indicates the bonding position and is bonded to two adjacent elements on the ring of the aryl ring or heteroaryl ring to which the group represented by formula (B10) or formula (B11) is bonded, respectively. Examples of compounds having such a structure include the following compounds.

[0352]

Chemical formula

[0353] The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, examples of one or more cycloalkanes condensed to one benzene ring (phenyl) are shown below. Cycloalkanes condensed to each other may be condensed as in formula (Cy-1-4) and formula (Cy-2-4). Even when the ring (group) to be condensed is another aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), or when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, the same applies.

[0354]

Chemical formula

[0355] At least one -CH in the cycloalkane 2 - may be substituted with -O-. For example, examples of one or more -CH in the cycloalkane condensed to one benzene ring (phenyl) substituted with -O- are shown below. Even when the ring (group) to be condensed is another aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), or when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, the same applies. 2 - may be substituted with -O-. For example, examples of one or more -CH in the cycloalkane condensed to one benzene ring (phenyl) substituted with -O- are shown below. Even when the ring (group) to be condensed is another aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), or when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, the same applies.

[0356]

Chemical formula

[0357] At least one hydrogen in the cycloalkane may be substituted, and examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen. The details of these can be cited from the description of the first substituent mentioned above. Among these substituents, alkyl (for example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), halogen (for example, fluorine), and deuterium are preferable. Also, when cycloalkyl is substituted, it may be in a substitution form that forms a spiro structure, and an example of this is shown below.

[0358] [Chemical formula]

[0359] As other forms of cycloalkane condensation, polycyclic aromatic compounds represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) and their multimers are, for example, >N-R where R is an aryl condensed with a cycloalkane, a diarylamino condensed with a cycloalkane (condensed to this aryl moiety), a carbazolyl condensed with a cycloalkane (condensed to this benzene ring moiety), or a benzocarbazolyl condensed with a cycloalkane (condensed to this benzene ring moiety). Examples of the "diarylamino" include the groups described as the above-mentioned "first substituent".

[0360] Furthermore, as more specific examples, R in the polycyclic aromatic compounds represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) and their multimers 2 is, for example, a diarylamino condensed with a cycloalkane (condensed to this aryl moiety) or a carbazolyl condensed with a cycloalkane (condensed to this benzene ring moiety).

[0361] As a more specific example of the polycyclic aromatic compound represented by the formula (2), for example, compounds represented by the following formulas can be mentioned. In the following formulas, "Me" represents methyl, "tBu" represents t-butyl, "iPr" represents isopropyl, "Ph" represents phenyl, "tAm" represents t-amyl (tertiary pentyl), and "D" represents deuterium.

[0362]

Chemical formula

[0363]

Chemical formula

[0364]

Chemical formula

[0365]

Chemical formula

[0366]

Chemical formula

[0367]

Chemical formula

[0368]

Chemical formula

[0369]

Chemical formula

[0370]

Chemical formula

[0371]

Chem.

[0372]

Chem.

[0373]

Chem.

[0374]

Chem.

[0375]

Chem.

[0376]

Chem.

[0377]

Chem.

[0378]

Chem.

[0379]

Chem.

[0380]

Chem.

[0381] [Chemistry]

[0382] [Chemistry]

[0383] [Chemistry]

[0384] [Chemistry]

[0385] [Chemistry]

[0386] [Chemistry]

[0387] [Chemistry]

[0388] [Chemistry]

[0389] [Chemistry]

[0390] [Chemistry]

[0391] [Chemistry]

[0392]

Chem.

[0393]

Chem.

[0394]

Chem.

[0395]

Chem.

[0396]

Chem.

[0397]

Chem.

[0398]

Chem.

[0399]

Chem.

[0400]

Chem.

[0401]

Chem.

[0402]

Chem.

[0403]

Chem.

[0404]

Chem.

[0405] 1-2-2. Method for producing a polycyclic aromatic compound represented by formula (2) and its multimer The polycyclic aromatic compound represented by formula (2) and its multimer can be synthesized, for example, by the method disclosed as "Method for producing polycyclic aromatic compound represented by formula (2) and its multimer" in International Publication No. 2019 / 009052.

[0406] 1-3. Light-emitting layer The light-emitting layer may be either a single layer or a plurality of layers, and is formed by a light-emitting layer material (host material, dopant material) respectively. The host material may be one compound represented by formula (1), a combination of two or more compounds represented by formula (1), or 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 compound represented by formula (1) or a combination of two or more compounds represented by formula (1). Further, the dopant material may be one compound represented by formula (2), a combination of two or more compounds represented by formula (2), or 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 compound represented by formula (2) or a combination of two or more compounds represented by formula (2).

[0407] The dopant material may be contained in the whole host material or partially contained therein. As the doping method, it can be formed by co-evaporation with the host material, but it may be co-evaporated after mixing with the host material in advance.

[0408] The usage amount of the host material varies depending on the type of the host material and may be determined according to the characteristics of the host material. The guideline for the usage amount of the host material is preferably 50 to 99.999% by mass of the total material for the light-emitting layer, more preferably 80 to 99.95% by mass, and still more preferably 90 to 99.9% by mass.

[0409] The usage amount of the dopant material varies depending on the type of the dopant material and may be determined according to the characteristics of the dopant material. The guideline for the usage amount of the dopant is preferably 0.001 to 50% by mass of the total material for the light-emitting layer, more preferably 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass. If it is within the above range, for example, it is preferable in that the concentration quenching phenomenon can be prevented.

[0410] Examples of the host material that can be used in combination with the compound represented by formula (1) include condensed ring derivatives such as pyrene and dibenzocrisene, which have been known as emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0411] Examples of the dopant material that can be used in combination with the compound represented by formula (2) include condensed ring derivatives such as anthracene and pyrene, which have been known as emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0412] 2. Electron injection layer and electron transport layer in an organic electroluminescent device The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 serves 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 transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more kinds of electron transport and injection materials, or by a mixture of an electron transport and injection material and a polymer binder.

[0413] The electron injection / transport layer is a layer that controls the injection and further transport of electrons from the cathode. It is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For this purpose, it is preferably a material having a large electron affinity, a large electron mobility, excellent stability, and a low occurrence of trap impurities during manufacturing and use. However, when considering the transport balance of holes and electrons, if it mainly plays a role in efficiently preventing holes from the anode from flowing to the cathode without recombination, even if the electron transport ability is not so high, the effect of improving the light emission efficiency is equivalent to that of a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently prevent the movement of holes.

[0414] As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, it can be arbitrarily selected and used from compounds conventionally used as electron transfer compounds in photoconductive materials and known compounds used in the electron injection layer and the electron transport layer of organic EL elements.

[0415] As the material used for the electron transport layer or the electron injection layer, it is preferable to contain at least one selected from compounds composed of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, aryl nitrile derivatives, and indole derivatives can be mentioned. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0416] Also, specific examples of other electron transfer compounds include borane derivatives, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (such as 2,2’-bis(benzo[h]quinolin-2-yl)-9,9’-spirobifluorene), imidazopyridine derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4’-(2,2’:6’,2”-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives, etc.

[0417] Also, metal complexes having electron-accepting nitrogen can also be used, for example, hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes, etc.

[0418] The above-mentioned materials can be used alone, or they can be used in combination with different materials.

[0419] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0420] <Borane derivative> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and details thereof are disclosed in Japanese Patent Application Laid-Open No. 2007-27587. [Chemical formula]

[0421] In formula (ETM-1), R 11 and R 12 are each independently hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen-containing heterocycle which may be substituted, or cyano, and at least one of them; R 13 ~R 16 are each independently alkyl which may be substituted, cycloalkyl which may be substituted, or aryl which may be substituted; X is arylene which may be substituted; Y is aryl having 16 or less carbon atoms which may be substituted, substituted boryl, or carbazolyl which may be substituted; and n is each independently an integer of 0 to 3. In addition, examples of the substituent in the case of "which may be substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0422] Among the compounds represented by formula (ETM-1), the compounds represented by the following formula (ETM-1-1) and the compounds represented by the following formula (ETM-1-2) are preferred.

Chemical formula

[0423] In formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, and R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, X 1 is optionally substituted arylene having 20 or fewer carbon atoms, n is an integer independently ranging from 0 to 3, and m is an integer independently ranging from 0 to 4. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0424]

Chemical formula

[0425] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16is, independently of each other, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, and X 1 is optionally substituted arylene having 20 or fewer carbon atoms, and n is, independently of each other, an integer of 0 to 3. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl, and the like.

[0426] X 1 Specific examples of X include divalent groups represented by any of the following formulas (X-1) to (X-9).

Chemical formula

[0427] Specific examples of this borane derivative include, for example, the following compounds.

Chemical formula

[0428] This borane derivative can be produced using known raw materials and known synthesis methods.

[0429] <Pyridine derivative> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

Chemical formula

[0430] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer from 1 to 4.

[0431] In formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0432] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and R 11 and R 12 may combine to form a ring.

[0433] In each formula, the "pyridine-based substituent" is any one of the following formulas (Py-1) to (Py-15) (the * in the formula represents the bonding position), and the pyridine-based substituents may each independently be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl, etc., and methyl is preferred. Also, the pyridine-based substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or naphthylene group.

[0434]

Chemical formula

[0435] The pyridine-based substituent is any one of formulas (Py-1) to (Py-15), and among these, it is preferably any one of the following formulas (Py-21) to (Py-44) (* in the formula represents the bonding position).

Chemical formula

[0436] At least one hydrogen in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine-based substituents" in formulas (ETM-2-1) and (ETM-2-2) may be replaced with aryl.

[0437] R 11 ~R 18 The "alkyl" in R~R may be either straight-chain or branched-chain, for example, straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms). Even more preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms).

[0438] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

[0439] As the C1-C4 alkyl substituting the pyridine-based substituent, the description of the above alkyl can be cited.

[0440] R 11 ~R 18 Examples of "cycloalkyl" in R~R include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl, and the like.

[0441] R 11 ~R 18 Examples of "aryl" in R~R include preferred aryl having 6 to 30 carbon atoms, more preferred aryl having 6 to 18 carbon atoms, even more preferred aryl having 6 to 14 carbon atoms, and particularly preferred aryl having 6 to 12 carbon atoms.

[0442] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl which is a monocyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, acenaphthylen-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, and the like.

[0443] Preferred "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

[0444] R in formula (ETM-2-2) 11 and R 12 may be bonded to form a ring. As a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0445] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0446] This pyridine derivative can be produced using known raw materials and known synthetic methods.

[0447] <Fluoranthene derivative> The fluoranthene derivative is a compound represented by, for example, the following formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0448] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0449] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0450] [BO-based derivative] The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4). [Chemical formula]

[0451] R 61 ~R 71 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0452] Also, R 61 ~R 71Adjacent groups among them may combine with each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring or c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0453] Also, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with halogen or deuterium.

[0454] Regarding the description of the substituents and ring formation forms in formula (ETM-4), the description of the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.

[0455] Specific examples of this BO-based derivative include, for example, the following compounds.

Chemical formula

[0456] This BO-based derivative can be produced using known raw materials and known synthesis methods.

[0457] <Anthracene derivative> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5).

Chemical formula

[0458] Ar 1 Each independently is a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0459] Ar 2Each is independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of the "aryl having 6 to 20 carbon atoms" include phenyl which is a monocyclic aryl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-)cumyl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-)naphthyl which is a condensed bicyclic aryl, terphenyl (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) which is a tricyclic aryl, condensed tricyclic aryls such as anthracene-(1-, 2-, 9-)yl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, condensed tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, and condensed pentacyclic aryls such as perylene-(1-, 2-, 3-)yl. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0460] R 1 ~R 4 Each is independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or aryl having 6 to 20 carbon atoms.

[0461] R 1 ~R 4 For the alkyl group having 1 to 6 carbon atoms in R, it may be either a straight-chain or a branched-chain. That is, it is a straight-chain alkyl group having 1 to 6 carbon atoms or a branched-chain alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (a branched-chain alkyl group having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, etc. Among them, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl are preferred, and methyl, ethyl, or t-butyl are more preferred.

[0462] R 1 ~R 4 Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in R include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl, etc.

[0463] R 1 ~R 4 For the aryl group having 6 to 20 carbon atoms in R, an aryl group having 6 to 16 carbon atoms is preferred, an aryl group having 6 to 12 carbon atoms is more preferred, and an aryl group having 6 to 10 carbon atoms is particularly preferred. Specific examples of the "aryl group having 6 to 20 carbon atoms" include those cited as specific examples of the "aryl group having 6 to 20 carbon atoms" in Ar 2 Specific examples of the "aryl group having 6 to 20 carbon atoms" in can be cited. Preferred "aryl groups having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, or naphthyl. More preferably, they are phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5'-yl. Even more preferably, they are phenyl, biphenylyl, 1-naphthyl, or 2-naphthyl. Most preferably, it is phenyl.

[0464] Specific examples of these anthracene derivatives include, for example, the following compounds.

Chemical formula

[0465] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0466] <Benzofluorene derivative> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Chemical formula

[0467] Ar 1 is, independently of each other, an aryl having 6 to 20 carbon atoms, and the description of "aryl having 6 to 20 carbon atoms" in Ar 2 in formula (ETM-5) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylenyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0468] Ar 2 is, independently of each other, hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ars 2 may be bonded to form a ring.

[0469] Ar 2The "alkyl" herein may be either straight-chain or branched-chain, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms). Even more preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0470] Ar 2 The "cycloalkyl" herein includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, and the like.

[0471] Ar 2 The "aryl" herein, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, even more preferably aryl having 6 to 14 carbon atoms, and particularly preferably aryl having 6 to 12 carbon atoms.

[0472] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, and the like.

[0473] Two Ars 2 may be bonded to form a ring. As a result, a cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0474] Specific examples of this benzofluorene derivative include, for example, the following compounds.

Chemical formula

[0475] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0476] <Phosphine oxide derivative> The phosphine oxide derivative is a compound represented by, for example, the following formula (ETM-7-1). Details are also described in International Publication No. 2013 / 079217 and International Publication No. 2013 / 079678.

Chemical formula

[0477] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms, R 7 and R 8 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl, cycloalkyl, and the like.

[0478] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

Chemical formula

[0479] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether group, arylthioether group, aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a condensed ring formed between adjacent substituents.

[0480] Ar 1 may be the same or different and is arylene or heteroarylene. Ar 2 may be the same or different and is aryl or heteroaryl. However, Ar 1 and Ar 2 at least one of which has a substituent or forms a condensed ring with an adjacent substituent. n is an integer from 0 to 3. When n is 0, there is no unsaturated structure portion, and when n is 3, R 1 does not exist.

[0481] Among these substituents, "alkyl" refers to a saturated aliphatic hydrocarbon group such as methyl, ethyl, propyl, butyl, etc., which may be unsubstituted or substituted. There are no particular restrictions on the substituents in the case of substitution, and examples include alkyl, aryl, heterocyclic groups, etc. This also applies to the following descriptions. Also, the number of carbon atoms in the alkyl is not particularly limited, but from the viewpoints of availability and cost, it is usually in the range of 1 to 20.

[0482] Also, "cycloalkyl" refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl part is not particularly limited, but it is usually in the range of 3 to 20.

[0483] Also, "aralkyl" refers to an aromatic hydrocarbon group via an aliphatic hydrocarbon such as benzyl, phenylethyl, etc., and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic part is not particularly limited, but it is usually in the range of 1 to 20.

[0484] Also, "alkenyl" refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as vinyl, allyl, butadienyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but it is usually in the range of 2 to 20.

[0485] Also, "cycloalkenyl" refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as cyclopentenyl, cyclopentadienyl, cyclohexene, etc., which may be unsubstituted or substituted.

[0486] Also, "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as ethynyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but it is usually in the range of 2 to 20.

[0487] In addition, alkoxy refers to, for example, an aliphatic hydrocarbon group via an ether bond such as methoxy, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0488] In addition, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is substituted with a sulfur atom.

[0489] In addition, cycloalkylthio is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is substituted with a sulfur atom.

[0490] In addition, an aryl ether group refers to, for example, an aromatic hydrocarbon group via an ether bond such as phenoxy, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0491] In addition, an aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

[0492] In addition, aryl refers to, for example, aromatic hydrocarbon groups such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, pyrenyl, etc. The aryl may be unsubstituted or substituted. The number of carbon atoms in the aryl is not particularly limited, but is usually in the range of 6 to 40.

[0493] In addition, a heterocyclic group refers to, for example, a cyclic structural group having an atom other than carbon such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., and this may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0494] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0495] The formyl, carbonyl, and amino groups can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

[0496] In addition, the aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocycle may be unsubstituted or substituted.

[0497] Silyl refers to, for example, a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. Also, the number of silicon atoms is usually 1 to 6.

[0498] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 and the like, which are conjugated or non-conjugated condensed rings formed therebetween. Here, when n is 1, two R 1 may form a conjugated or non-conjugated condensed ring with each other. These condensed rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may further condense with another ring.

[0499] Specific examples of this phosphine oxide derivative include, for example, the following compounds.

Chemical formula

[0500] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0501] <Pyrimidine derivative> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011 / 021689.

Chemical formula

[0502] Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably 2 or 3.

[0503] Examples of the "aryl" in the "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms.

[0504] Specific examples of "aryl" include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenylyl which is a tricyclic aryl (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), acenaphthylen-(1-, 3-, 4-, 5-) yl, fluorene-(1-, 2-, 3-, 4-, 9-) yl, phenalen-(1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl which are condensed tricyclic aryls, quaterphenylyl which is a tetracyclic aryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene-(1-, 2-) yl, pyrene-(1-, 2-, 4-) yl, naphthacene-(1-, 2-, 5-) yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-) yl, pentacene-(1-, 2-, 5-, 6-) yl which are condensed pentacyclic aryls, and the like.

[0505] Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl also include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0506] Specific heteroaryls include, for example, 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, cinnolyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, and the like.

[0507] Also, the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl or heteroaryl, respectively.

[0508] Specific examples of this pyrimidine derivative include, for example, the following compounds.

Chemical formula

[0509] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0510] <Aryl nitrile derivative> The aryl nitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of them are bonded by a single bond or the like. Details are described in US Patent Application Publication No. 2014 / 0197386.

Chemical formula

[0511] Ar niFrom the perspective of fast electron transport property, it is preferable to have a large number of carbon atoms, while from the perspective of high T1, it is preferable to have a small number of carbon atoms. Ar ni Specifically, for use in the layer adjacent to the light-emitting layer, it is preferably a high T1, and is an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 14 carbon atoms, more preferably an aryl having 6 to 10 carbon atoms. Also, the substitution number n of the nitrile group is preferably large from the perspective of high T1, and preferably small from the perspective of high S1. Specifically, the substitution number n of the nitrile group is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

[0512] Ar is each independently an optionally substituted aryl or an optionally substituted heteroaryl. From the perspectives of high S1 and high T1, it is preferably a donor heteroaryl, and for use as an electron transport layer, it is preferably a donor heteroaryl with a small number. From the perspective of charge transport property, an aryl or heteroaryl with a large number of carbon atoms is preferred, and it is preferred to have a large number of substituents. Specifically, the substitution number m of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 1 to 2.

[0513] Examples of the "aryl" in the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0514] Specific "aryl" includes phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenyl (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) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quarterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quarterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, etc.

[0515] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Also, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0516] Specific heteroaryl groups include, for example, 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, cinnolyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, and the like.

[0517] In addition, the above aryl and heteroaryl groups may be substituted, and may be substituted with, for example, the above aryl or heteroaryl groups, respectively.

[0518] The aryl nitrile derivative may be a multimer in which the compound represented by formula (ETM-9) is bonded through a plurality of single bonds or the like. In this case, in addition to the single bond, it may be bonded through an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring).

[0519] Specific examples of this aryl nitrile derivative include, for example, the following compounds.

Chemical formula

[0520] This aryl nitrile derivative can be produced using known raw materials and known synthetic methods.

[0521] <Triazine derivative> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Patent Application Publication No. 2011 / 0156013.

Chemical formula

[0522] Each Ar is independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

[0523] Examples of the "aryl" in the "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0524] Specific examples of the "aryl" include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenyl (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) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quaterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, etc.

[0525] Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, still more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Further, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0526] Specific heteroaryl groups include, for example, 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, cinnolyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, and the like.

[0527] In addition, the above aryl and heteroaryl groups may be substituted, and may be substituted, for example, with the above aryl or heteroaryl groups, respectively.

[0528] Specific examples of this triazine derivative include, for example, the following compounds.

Chemical formula

[0529] This triazine derivative can be produced using known raw materials and known synthetic methods.

[0530] <Benzimidazole derivative> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

Chemical formula

[0531] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "benzimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in Formula (ETM-2), Formula (ETM-2-1) and Formula (ETM-2-2) is replaced by benzimidazolyl. At least one hydrogen in the benzimidazole derivative may be replaced by deuterium.

[0532]

Chemical formula

[0533] R in the above benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms, and the description of R 11 in Formula (ETM-2-1) and Formula (ETM-2-2) can be cited.

[0534] φ is preferably further an anthracene ring or a fluorene ring. In this case, the structure can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2), and R 11 ~R 18 in each formula can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2). Also, in Formula (ETM-2-1) or Formula (ETM-2-2), the two pyridine-based substituents are described in a bonded form. When replacing these with benzimidazole-based substituents, both pyridine-based substituents may be replaced by benzimidazole-based substituents (i.e., n = 2), or either one of the pyridine-based substituents may be replaced by a benzimidazole-based substituent and the other pyridine-based substituent may be replaced by R 11 ~R 18 (i.e., n = 1). Further, for example, R 11 ~R 18Replace at least one of them with a benzimidazole-based substituent to obtain a "pyridine-based substituent" as R 11 ~R 18 which may be replaced.

[0535] Specific examples of this benzimidazole derivative include, for example, 1-phenyl-2-(4-(10-phenylanthracen-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-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.

[0536]

Chemical formula

[0537] This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0538] <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.

[0539] [Chemical formula]

[0540] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer from 1 to 4.

[0541] Each R in each formula 11 ~R 18 is independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). In formula (ETM-12-1), one of R 11 ~R 18 forms a bond with φ which is an aryl ring.

[0542] At least one hydrogen in each phenanthroline derivative may be replaced by deuterium.

[0543] R 11 ~R 18 For the alkyl, cycloalkyl and aryl in R 11 ~R 18 in formula (ETM-2), the description of R

[0544] [Chemical formula]

[0545] Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6-di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10-phenanthrolin-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene, and compounds represented by the following structural formula.

[0546]

Chem.

[0547] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0548] <Quinolinol-based metal complex> The quinolinol-based metal complex is, for example, a compound represented by the following formula (ETM-13).

Chem.

[0549] Specific examples of the quinolinol-based metal complex include lithium 8-quinolinolate, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(4-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,3-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-di-t-butylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-trimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,5,6-tetramethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinolato)(2-naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(2-phenylphenolato)aluminum, bis(2,(4-Dimethyl-8-quinolinolato)(3-phenylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(4-phenylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3,5-di-t-butylphenolato)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, 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, bis(10-hydroxybenzo[h]quinoline)beryllium, etc. can be mentioned.,

[0550] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0551] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [Chemical formula] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [Chemical formula]

[0552] Each φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "thiazole-based substituent" and "benzothiazole-based substituent" are substituents in which the pyridyl in the "pyridine-based substituent" in Formula (ETM-2), Formula (ETM-2-1) and Formula (ETM-2-2) is replaced by the following thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be replaced by deuterium.

[0553]

Chemical formula

[0554] φ is more preferably an anthracene ring or a fluorene ring. In this case, the structure can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2), and R 11 ~R 18 in each formula can cite the description in Formula (ETM-2-1) or Formula (ETM-2-2). Also, although Formula (ETM-2-1) or Formula (ETM-2-2) describes the form in which two pyridine-based substituents are bonded, when replacing these with thiazole-based substituents (or benzothiazole-based substituents), both pyridine-based substituents may be replaced with thiazole-based substituents (or benzothiazole-based substituents) (i.e., n = 2), or either one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n = 1). Further, for example, at least one of R 11 ~R 18 in Formula (ETM-2-1) may be replaced with a thiazole-based substituent (or benzothiazole-based substituent) to replace the "pyridine-based substituent" with R 11 ~R 18 as well.

[0555] These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0556] <Sylol derivative> The sylol derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in JP-A-9-194487. [Chemical formula]

[0557] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, and these may be substituted. For details of these groups, the descriptions in formulas (1) and (2) and further the description in formula (ETM-7-2) can be cited. Also, alkenyloxy and alkynyloxy are groups in which the alkyl part in alkoxy is replaced by alkenyl or alkynyl, and for details of these alkenyl and alkynyl, the description in formula (ETM-7-2) can be cited. Further, X and Y may be bonded to form a cycloalkyl ring (and a ring in which a part thereof is unsaturated), and for details of this cycloalkyl ring, the description of cycloalkyl in formulas (1) and (2) can be referred to.

[0558] R 1 ~R 4Each independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen and may form a condensed ring with adjacent substituents.

[0559] R 1 ~R 4 For the details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the descriptions in formula (1) and formula (2) can be cited.

[0560] R 1 ~R 4 For the details of alkyl, aryl and alkoxy in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in, the descriptions in formula (1) and formula (2) can also be cited.

[0561] As the silyl group, there are an unsubstituted silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with aryl, alkyl or cycloalkyl. A trisubstituted silyl group is preferred, and examples thereof include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl and alkyldicycloalkylsilyl. For the details of aryl, alkyl and cycloalkyl in these, the descriptions in formula (1) and formula (2) can be cited.

[0562] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 and the like, which are conjugated or non-conjugated condensed rings formed therebetween. These condensed rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may further be condensed with another ring.

[0563] However, preferably, when R 1 and R 4 are phenyl, X and Y are not alkyl or phenyl. Also preferably, when R 1 and R 4 are thienyl, X and Y are alkyl, and when R 2 and R 3 are alkyl, aryl, alkenyl or cycloalkyl in which R 2 and R 3 are bonded to form a ring, they do not satisfy the structure at the same time. Also preferably, when R 1 and R 4 are silyl, R 2 , R 3 , X and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms. Also preferably, when R 1 and R 2 form a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0564] These silyl derivatives can be produced using known raw materials and known synthesis methods.

[0565] <Azoline derivative> The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in International Publication No. 2017 / 014226.

Chemical formula

[0566] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen of φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms. Y is, independently of each other, -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms. R 1 ~R 5 are each independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that any one of Ar in the >N-Ar and R 1 ~R 5 is a site that binds 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).

[0567]

Chemical formula

[0568] In formula (L-1), X 1 ~X 6is each independently =CR 6 - or =N-, and X 1 ~X 6 at least two of which are =CR 6 -, and X 1 ~X 6 two of the =CR 6 R in 6 is a site that binds to φ or an azoline ring, and the other =CR 6 R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N-, and X 7 ~X 14 at least two of which are =CR 6 -, and X 7 ~X 14 two of the =CR 6 R in 6 is a site that binds to φ or an azoline ring, and the other =CR 6 R in 6 is hydrogen, At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms, m is an integer from 1 to 4. When m is from 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0569] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2).

Chemical formula

[0570] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen of φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms. In formula (ETM-16-1), Y is, independently of each other, -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms. In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are the same, and also R 3 and R 4 are the same. In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are the same, and also R 3 and R 4 are the same. In formula (ETM-16-1) and formula (ETM-16-2), L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

[0571]

Chemical formula

[0572] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N-, and X1 ~X 6 At least two of them are =CR 6 -, and X 1 ~X 6 Two of =CR 6 The R in 6 is a site that binds to a phenyl or azoline ring, and the R in the other =CR 6 The R in 6 is hydrogen, and In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N-, and X 7 ~X 14 At least two of them are =CR 6 -, and X 7 ~X 14 Two of =CR 6 The R in 6 is a site that binds to a phenyl or azoline ring, and the R in the other =CR 6 The R in 6 is hydrogen, and At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. m is an integer from 1 to 4. When m is from 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0573] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formula (φ1-1) to formula (φ1-18), divalent groups represented by the following formula (φ2-1) to formula (φ2-34), trivalent groups represented by the following formula (φ3-1) to formula (φ3-3), and tetravalent groups represented by the following formula (φ4-1) to formula (φ4-2). At least one hydrogen of φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms.

[0574]

Chem.

[0575]

Chem.

[0576]

Chem.

[0577] In the formula, Z is >CR 2 , >N-Ar, >N-L, -O- or -S-, and R in >CR 2 is, independently of one another, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and the Rs may be bonded to one another to form a ring. Ar in >N-Ar is aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and L in >N-L is L in formula (ETM-16), formula (ETM-16-1) or formula (ETM-16-2). * in the formula represents the bonding position.

[0578] 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 may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms or heteroaryl having 2 to 10 carbon atoms.

[0579] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0580] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are the same, R 3 and R 4 are the same, and also R 1 ~R 4 do not all simultaneously become hydrogen, and m is 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[0581] Specific examples of the azoline derivative include, for example, the following compounds. In the structural formula, "Me" represents methyl.

Chemical formula

Chemical formula

[0582] More preferably, φ is selected from the group consisting of divalent groups represented by the following formula (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33), and formula (φ2-34), and at least one hydrogen of φ may be substituted with aryl having 6 to 18 carbon atoms.

Chemical formula

[0583] L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 2 to 14 carbon atoms. In >N-Ar as Y, Ar is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of the Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, or an aryl having 6 to 10 carbon atoms. R 1 ~R 4 are each independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are the same, R 3 and R 4 are the same, and also R 1 ~R 4 do not all become hydrogen simultaneously, and m is 2, and the group formed by the azoline ring and L is the same.

[0584] Other specific examples of the azoline derivative include, for example, the following compounds. In the structural formula, "Me" represents methyl.

Chemical formula

[0585] Regarding the details of the alkyl, cycloalkyl, aryl, or heteroaryl in the above formulas defining this azoline derivative, the descriptions in Formula (1) and Formula (2) can be cited.

[0586] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0587] <Reducing substance> The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As long as this reducing substance has a certain reducibility, various substances can be used. For example, 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. At least one selected from the group consisting of them can be preferably used.

[0588] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 - 2.5 eV), or Ba (2.52 eV). Those with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals of K, Rb, or Cs, even more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, an improvement in the emission luminance and a longer lifespan of the organic EL element can be achieved. Also, as reducing substances with a work function of 2.9 eV or less, combinations of two or more of these alkali metals are also preferred. In particular, combinations containing Cs, for example, combinations of Cs and Na, Cs and K, Cs and Rb, or combinations of Cs, Na, and K are preferred. By including Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, an improvement in the emission luminance and a longer lifespan of the organic EL element can be achieved.

[0589] 3. Substrate in an organic electroluminescent device The substrate 101 serves as a support for the organic EL element 100, and usually, quartz, glass, metal, plastic, etc. are used. The substrate 101 is formed in a plate shape, film shape, or sheet shape according to the purpose, and for example, a glass plate, metal plate, metal foil, plastic film, plastic sheet, etc. are used. Among these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, polysulfone are preferable. In the case of a glass substrate, soda-lime glass, alkali-free glass, etc. are used, and the thickness only needs to be sufficient to maintain mechanical strength, so for example, 0.2 mm or more is sufficient. As the upper limit value of the thickness, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, since it is better that there are fewer eluted ions from the glass, alkali-free glass is preferable, but soda-lime glass with a barrier coat such as SiO 2 etc. is also commercially available and can be used. Further, in order to enhance the gas barrier property of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side, and particularly when a plate, film, or sheet made of a synthetic resin with low gas barrier property is used as the substrate 101, it is preferable to provide a gas barrier film.

[0590] 4. Anode in an organic electroluminescent device The anode 102 serves to inject holes into the light-emitting layer 105. When a hole injection layer 103 and / or a 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 through these layers.

[0591] Examples of materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (such as aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (such as indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (such as copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from among the substances used as the anode of the organic EL element.

[0592] The resistance of the transparent electrode is not limited as long as a current sufficient for the light emission of the light-emitting element can be supplied, but it is desirable to have a low resistance from the viewpoint of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / square or less can function as an element electrode, but currently substrates with a resistance of about 10 Ω / square can also be supplied. Therefore, it is particularly desirable to use low-resistance products with a resistance of, for example, 100 to 5 Ω / square, preferably 50 to 5 Ω / square. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0593] 5. Hole injection layer and hole transport layer in an organic electroluminescent device The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves 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 each formed by laminating or mixing one or more hole injection / transport materials, or by a mixture of 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.

[0594] As a hole injection / transporting material, it is necessary 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 injection efficiency is high and the injected holes are efficiently transported. For this purpose, a material having a small ionization potential, a large hole mobility, excellent stability, and few impurities that cause traps during manufacturing and use is preferable.

[0595] As the material for forming the hole injection layer 103 and the hole transport layer 104, in the photoconductive material, any one can be selected and used from compounds conventionally used as hole charge transport materials, p-type semiconductors, and known materials used for the hole injection layer and the hole transport layer of organic EL elements. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino group in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4''-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, triphenylamine derivatives such as N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone-based compounds, benzofuran derivatives and 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, polysilane, etc. In the polymer system, polycarbonate, styrene derivatives, polyvinylcarbazole, and polysilane having the above monomer in the side chain are preferred, but it is not particularly limited as long as it can form a thin film necessary for the production of the light-emitting element, holes can be injected from the anode, and further holes can be transported.

[0596] Also, it is known that the conductivity of an organic semiconductor is strongly affected by its doping. Such an organic semiconductor matrix material is composed of a compound with good electron-donating properties or a compound with good electron-accepting properties. For doping with an electron-donating substance, strong electron acceptors such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4TCNQ) are known (for example, refer to the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202 - 3204(1998)" and the literature "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729 - 731(1998)"). These generate so-called holes by the electron transfer process in an electron-donating base material (hole transport material). The conductivity of the base material changes considerably depending on the number and mobility of the holes. As matrix materials having hole transport characteristics, for example, benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Application Laid-Open No. 2005-167175).

[0597] 6. Cathode in an organic electroluminescent device The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.

[0598] The material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, and the same materials as those for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) are preferred. In order to improve the device characteristics by increasing the electron injection efficiency, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this point, for example, a method of doping a trace amount of lithium, cesium, or magnesium into the organic layer and using a highly stable electrode is known. Other dopants such as inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, it is not limited to these.

[0599] Furthermore, for electrode protection, it is preferable to stack metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, etc. The manufacturing methods of these electrodes are not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0600] 7. Binder that may be used in each layer of an organic electroluminescent device The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer independently, but can also be used by dispersing them in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, etc., or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc.

[0601] <<Method for manufacturing an organic electroluminescent device>> Each layer constituting the organic EL device can be formed by forming a thin film by methods such as vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, inkjet method, spin coating method or casting method, coating method, etc. There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately set according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillator type film thickness measuring device, etc. When thinning by the vapor deposition method, the vapor deposition conditions vary depending on the type of material, the intended crystal structure and association structure of the film, etc. The vapor deposition conditions are generally preferably set appropriately in the range of boat heating temperature +50 to +400 °C, vacuum degree 10 -6 ~10 -3 Pa, deposition rate 0.01 to 50 nm / second, substrate temperature -150 to +300 °C, film thickness 2 nm to 5 μm.

[0602] Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element composed of an anode / hole injection layer / hole transport layer / light-emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described. After forming a thin film of an anode material on a suitable substrate by a vapor deposition method or the like to fabricate an anode, thin films of a hole injection layer and a hole transport layer are formed on this anode. A host material and a dopant material are co-evaporated thereon to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on this light-emitting layer, and further a thin film made of a cathode material is formed by a vapor deposition method or the like to form a cathode, whereby the target organic EL element can be obtained. In addition, in the manufacture of the above-described organic EL element, it is also possible to reverse the manufacturing order and manufacture in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0603] When a DC voltage is applied to the organic EL element thus obtained, it may be applied with the anode as the + and the cathode as the - polarity. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, and both). Further, this organic EL element also emits light when a pulse current or an alternating current is applied. The waveform of the alternating current to be applied may be arbitrary.

[0604] <<Application Examples of Organic Electroluminescent Elements>> Further, the present invention can also be applied to a display device including an organic EL element or a lighting device including an organic EL element. A display device or a lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment and a known driving device, and can be driven by appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0605] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (see, for example, Japanese Patent Application Laid-Open Nos. 10-335066, 2003-321546, 2004-281086, etc.). Examples of the display method of the display include, for example, matrix and / or segment methods. Note that matrix display and segment display may coexist in the same panel.

[0606] A matrix refers to a two-dimensional arrangement of pixels for display in a grid or mosaic pattern, etc., and characters and images are displayed by a set of pixels. The shape and size of the pixels are determined by the application. For example, for image and character display on personal computers, monitors, and televisions, square pixels with a side length of 300 μm or less are usually used. In the case of a large display such as a display panel, pixels with a side length on the order of mm are used. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green, and blue pixels are arranged for display. In this case, typically, there are delta type and stripe type. And as the driving method of this matrix, either a line sequential driving method or an active matrix may be used. The line sequential driving has the advantage of a simple structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is also necessary to use them appropriately depending on the application.

[0607] In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is caused to emit light. For example, time and temperature display on digital clocks and thermometers, operation state display on audio devices and electromagnetic cookers, and panel display of automobiles, etc. are given.

[0608] Examples of lighting devices include lighting devices for indoor lighting and the like, and backlights for liquid crystal display devices (see, for example, Japanese Patent Application Laid-Open Nos. 2003-257621, 2003-277741, 2004-119211, etc.). Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light spontaneously, and are used in liquid crystal display devices, clocks, audio devices, automotive panels, display boards, and signs. In particular, as a backlight for a personal computer application where thinning is an issue, especially in a liquid crystal display device, considering that a conventional type is composed of a fluorescent lamp and a light guide plate and thus it is difficult to make it thin, the backlight using the light-emitting element according to the present embodiment is characterized by being thin and lightweight.

Example

[0609] Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited thereto. First, a synthesis example of the compound used in the examples will be described below.

[0610] Synthesis Example (1-1): Synthesis of Compound (1-1)

Chemical formula

[0611] Compound (1-1) was synthesized according to the method described in International Publication No. 2006 / 003842.

[0612] Synthesis Example (1-2): Synthesis of Compound (1-12)

Chemical formula

[0613] Compound (1-12) was synthesized according to the method described in International Publication No. 2006 / 003842.

[0614] Synthesis Example (1-3): Synthesis of Compound (1-16)

Chemical formula

[0615] Compound (1-16) was synthesized according to the method described in WO 2006 / 003842.

[0616] Synthesis Example (1-4): Synthesis of Compound (1-47) [Chemical formula]

[0617] Compound (1-47) was synthesized according to the method described in WO 2006 / 003842.

[0618] Synthesis Example (1-5): Synthesis of Compound (1-153) [Chemical formula]

[0619] Compound (1-153) was synthesized according to the method described in WO 2006 / 003842.

[0620] Synthesis Example (1-6): Synthesis of Compound (1-255) [Chemical formula]

[0621] Compound (1-255) was synthesized according to the method described in WO 2006 / 003842.

[0622] Synthesis Example (1-7): Synthesis of Compound (1-263) [Chemical formula]

[0623] Compound (1-263) was synthesized according to the method described in WO 2006 / 003842.

[0624] Synthesis Example (1-8): Synthesis of Compound (1-319) [Chemical formula]

[0625] Compound (1-319) was synthesized according to the method described in International Publication No. WO 2006 / 003842.

[0626] Synthesis Example (1-9): Synthesis of Compound (1-454) [Chemical formula]

[0627] Compound (1-454) was synthesized by appropriately changing the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 496.

[0628] [Chemical formula]

[0629] Synthesis Example (1-10): Synthesis of Compound (1-457) [Chemical formula]

[0630] Compound (1-457) was synthesized by appropriately changing the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 596.

[0631] [Chemical formula]

[0632] Synthesis Example (1-11): Synthesis of Compound (1-456) [Chemical formula]

[0633] Compound (1-456) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 596.

[0634]

Chemical formula

[0635] Synthesis Example (1-12): Synthesis of Compound (1-490)

Chemical formula

[0636] Compound (1-490) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 546.

[0637]

Chemical formula

[0638] Synthesis Example (1-13): Synthesis of Compound (1-493)

Chemical formula

[0639] Compound (1-493) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 646.

[0640]

Chemical formula

[0641] Synthesis Example (1-14): Synthesis of Compound (1-492)

Chemical formula

[0642] Compound (1-492) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 646.

[0643]

Chemical formula

[0644] Synthesis Example (1-15): Synthesis of Compound (1-641)

Chemical formula

[0645] Compound (1-641) was synthesized according to the method described in International Publication No. 2009 / 142230.

[0646] Synthesis Example (1-16): Synthesis of Compound (1-646)

Chemical formula

[0647] Compound (1-646) was synthesized according to the method described in International Publication No. 2009 / 142230.

[0648] Synthesis Example (1-17): Synthesis of Compound (1-649)

Chemical formula

[0649] Compound (1-649) was synthesized according to the method described in International Publication No. 2009 / 142230.

[0650] Synthesis Example (1-18): Synthesis of Compound (1-640)

Chemical formula

[0651] Compound (1-640) was synthesized according to the method described in WO 2009 / 142230.

[0652] Synthesis Example (1-19): Synthesis of Compound (1-535)

Chemical formula

[0653] Compound (1-535) was synthesized according to the method described in WO 2009 / 142230.

[0654] Synthesis Example (1-20): Synthesis of Compound (1-534)

Chemical formula

[0655] Compound (1-534) was synthesized according to the method described in WO 2009 / 142230.

[0656] Synthesis Example (1-21): Synthesis of Compound (1-677)

Chemical formula

[0657] Compound (1-677) was synthesized by appropriately changing the raw material compounds of the method described in WO 2009 / 142230. EI-MS: m / z = 708.

[0658] Synthesis Example (1-22): Synthesis of Compound (1-682)

Chemical formula

[0659] Compound (1-682) was synthesized by appropriately modifying the compounds of the raw materials of the method described in International Publication No. WO 2009 / 142230. EI-MS: m / z = 784.

[0660] Synthesis Example (1-23): Synthesis of Compound (1-1334)

Chemical Structure

[0661] Compound (1-1334) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[0662]

Chemical Structure

[0663] Synthesis Example (1-24): Synthesis of Compound (1-1336)

Chemical Structure

[0664] Compound (1-1336) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[0665]

Chemical Structure

[0666] Synthesis Example (1-25): Synthesis of Compound (1-279)

Chemical Structure

[0667] Compound (1-279) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 737.

[0668]

Chem.

[0669] Synthesis Example (1 - 26): Synthesis of Compound (1 - 125)

Chem.

[0670] Compound (1 - 125) was synthesized according to the method described in International Publication No. WO 2006 / 003842.

[0671] Synthesis Example (1 - 27): Synthesis of Compound (1 - 155)

Chem.

[0672] Compound (1 - 155) was synthesized according to the method described in International Publication No. WO 2006 / 003842.

[0673] Synthesis Example (1 - 28): Synthesis of Compound (1 - 29)

Chem.

[0674] Compound (1 - 29) was synthesized according to the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 587.

[0675]

Chem.

[0676] Synthesis Example (1 - 29): Synthesis of Compound (1 - 276)

Chem.

[0677] Compound (1-276) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[0678]

Chemical formula

[0679] Synthesis Example (1-30): Synthesis of Compound (1-448)

Chemical formula

[0680] Compound (1-448) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 671.

[0681]

Chemical formula

[0682] Synthesis Example (1-31): Synthesis of Compound (1-13)

Chemical formula

[0683] Compound (1-13) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 658.

[0684]

Chemical formula

[0685] Synthesis Example (1-32): Synthesis of Compound (1-287)

Chemical formula

[0686] Compound (1-287) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 532.

[0687] [Chemical formula]

[0688] Synthesis Example (1-33): Synthesis of Compound (1-124) [Chemical formula]

[0689] Compound (1-124) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 482.

[0690] [Chemical formula]

[0691] Synthesis Example (1-34): Synthesis of Compound (1-4) [Chemical formula]

[0692] Compound (1-4) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 558.

[0693] [Chemical formula]

[0694] Synthesis Example (1-35): Synthesis of Compound (1-807) [Chemical formula]

[0695] Compound (1-807) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 546.

[0696]

Chemical formula

[0697] Synthesis Example (1-36): Synthesis of Compound (1-802)

Chemical formula

[0698] Compound (1-802) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 496.

[0699]

Chemical formula

[0700] Synthesis Example (1-37): Synthesis of Compound (1-2400)

Chemical formula

[0701] Compound (1-2400) was synthesized by appropriately modifying the compounds of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 532.

[0702]

Chemical formula

[0703] Synthesis Example (1-38): Synthesis of Compound (1-2401) [ka]

[0704] Compound (1-2401) was synthesized by appropriately changing the raw material compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z=482. [ka]

[0705] Synthesis Example (1-39): Synthesis of Compound (1-4133) Compound (1-4133) was synthesized by appropriately changing the raw material compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z=609.

[0706] [ka]

[0707] Synthesis Example (1-40): Synthesis of Compound (1-148) Compound (1-148) was synthesized by appropriately changing the raw material compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z=533.

[0708] [ka]

[0709] Synthesis Example (1-41): Synthesis of Compound (1-150) Compound (1-150) was synthesized by appropriately changing the raw material compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z=633.

[0710] [Chemistry]

[0711] Synthesis Example (1 - 42): Synthesis of Compound (1 - 136) Compound (1 - 136) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 533.

[0712] [Chemistry]

[0713] Synthesis Example (1 - 43): Synthesis of Compound (1 - 4155) Compound (1 - 4155) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 583.

[0714] [Chemistry]

[0715] Synthesis Example (1 - 44): Synthesis of Compound (1 - 3268) Compound (1 - 3268) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 573.

[0716] [Chemistry]

[0717] Synthesis Example (1 - 45): Synthesis of Compound (1 - 4114) Compound (1 - 4114) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 573.

[0718]

Chem.

[0719] Synthesis Example (1 - 46): Synthesis of Compound (1 - 4121) Compound (1 - 4121) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 573.

[0720]

Chem.

[0721] Synthesis Example (1 - 47): Synthesis of Compound (1 - 4119) Compound (1 - 4119) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 573.

[0722]

Chem.

[0723] Synthesis Example (1 - 48): Synthesis of Compound (1 - 4120) Compound (1 - 4120) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 663.

[0724]

Chem.

[0725] Synthesis Example (1 - 49): Synthesis of Compound (1 - 4107) Compound (1 - 4107) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 663.

[0726] [Chemical formula]

[0727] Synthesis Example (1 - 50): Synthesis of Compound (1 - 4317) Compound (1 - 4317) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 583.

[0728] [Chemical formula]

[0729] Synthesis Example (1 - 51): Synthesis of Compound (1 - 4327) Compound (1 - 4327) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 633.

[0730] [Chemical formula]

[0731] Synthesis Example (1 - 52): Synthesis of Compound (1 - 3991) Compound (1 - 3991) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 573.

[0732] [Chemical formula]

[0733] Synthesis Example (1 - 53): Synthesis of Compound (1 - 2984) Compound (1-2984) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0734]

Chemical formula

[0735] Synthesis Example (1-54): Synthesis of Compound (1-3452) Compound (1-3452) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[0736]

Chemical formula

[0737] Synthesis Example (1-55): Synthesis of Compound (1-2883) Compound (1-2883) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[0738]

Chemical formula

[0739] Synthesis Example (1-56): Synthesis of Compound (1-4205) Under a nitrogen atmosphere, the intermediate (I-2) (1.0 g) was dissolved in toluene (100 ml), and the intermediate (I-1) (1.0 g), potassium carbonate (1.4 g), tetrabutylammonium bromide (TBAB, 0.4 g), and bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (Pd-132, 0.35 g) were added, and the mixture was stirred under heating and reflux for 5 hours. After the reaction, water was added to the reaction solution to stop the reaction, and then toluene was added for liquid separation extraction. Next, the organic layer was concentrated to obtain a crude product. The obtained crude product was purified by a silica gel short column (eluent: chlorobenzene) to obtain compound (1-4205) (0.85 g). EI-MS: m / z = 608.

[0740]

Chemical formula

[0741] Synthesis Example (1-57): Synthesis of Compound (1-4232) Compound (1-4232) was synthesized by appropriately changing the starting compounds in the method described in the above Synthesis Example (1-56). EI-MS: m / z = 658.

Chemical formula

[0742] Synthesis Example (1-58): Synthesis of Compound (1-4219) Compound (1-4219) was synthesized by appropriately changing the starting compounds in the method described in the above Synthesis Example (1-56). EI-MS: m / z = 608.

[0743]

Chemical formula

[0744] Synthesis Example (1-59): Synthesis of Compound (1-4254) Compound (1-4254) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 634.

[0745]

Chemical formula

[0746] Synthesis Example (1-60): Synthesis of Compound (1-4263) Compound (1-4263) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 658.

[0747]

Chemical formula

[0748] Synthesis Example (1-61): Synthesis of Compound (1-4271) Compound (1-4271) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 708.

[0749]

Chemical formula

[0750] Synthesis Example (1-62): Synthesis of Compound (1-2995) Compound (1-2995) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 648.

[0751]

Chemical formula

[0752] Synthesis Example (1-63): Synthesis of Compound (1-3005) Compound (1-3005) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 648.

[0753]

Chemical formula

[0754] Synthesis Example (1-64): Synthesis of Compound (1-3020) Compound (1-3020) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 750.

[0755]

Chemical formula

[0756] Synthesis Example (1-65): Synthesis of Compound (1-4204) Compound (1-4204) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 708.

[0757]

Chemical formula

[0758] Synthesis Example (1-66): Synthesis of Compound (1-4198) Compound (1-4198) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 788.

[0759]

Chemical formula

[0760] Synthesis Example (1-67): Synthesis of Compound (1-4280) Compound (1-4280) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 734.

[0761]

Chemical formula

[0762] Synthesis Example (1-68): Synthesis of Compound (1-3821) Compound (1-3821) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 838.

[0763]

Chemical formula

[0764] Synthesis Example (1-69): Synthesis of Compound (1-3078) Compound (1-3078) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 648.

[0765]

Chemical formula

[0766] Synthesis Example (1-70): Synthesis of Compound (1-4209) Compound (1-4209) was synthesized by appropriately changing the compounds of the raw materials in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 658.

[0767]

Chemical formula

[0768] Synthesis Example (1-71): Synthesis of Compound (1-4093) Compound (1-4093) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 609.

[0769] [Chemical formula]

[0770] Synthesis Example (1-72): Synthesis of Compound (1-4092) Compound (1-4092) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 811.

[0771] [Chemical formula]

[0772] Synthesis Example (1-73): Synthesis of Compound (1-2977) Compound (1-2977) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 699.

[0773] [Chemical formula]

[0774] Synthesis Example (1-74): Synthesis of Compound (1-4036) Compound (1-4036) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[0775] [Chemical formula]

[0776] Synthesis Example (1-75): Synthesis of Compound (1-4335) Compound (1-4335) was synthesized by appropriately changing the starting compounds in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 609.

[0777]

Chemical Structure

[0778] Synthesis Example (1-76): Synthesis of Compound (1-4347) Compound (1-4347) was synthesized by appropriately changing the starting compounds in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 609.

[0779]

Chemical Structure

[0780] Synthesis Example (1-77): Synthesis of Compound (1-4354) Compound (1-4354) was synthesized by appropriately changing the starting compounds in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 659.

[0781]

Chemical Structure

[0782] Synthesis Example (1-78): Synthesis of Compound (1-3751) Compound (1-3751) was synthesized by appropriately changing the starting compounds in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 649.

[0783]

Chemical Structure

[0784] Synthesis Example (1-79): Synthesis of Compound (1-4106) Compound (1-4106) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 609.

[0785]

Chemical Structure

[0786] Synthesis Example (1-80): Synthesis of Compound (1-3830) Compound (1-3830) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[0787]

Chemical Structure

[0788] Synthesis Example (1-81): Synthesis of Compound (1-3839) Compound (1-3839) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[0789]

Chemical Structure

[0790] Synthesis Example (1-82): Synthesis of Compound (1-4381) Compound (1-4381) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 583.

[0791]

Chemical Structure

[0792] Synthesis Example (1-83): Synthesis of Compound (1-4390) Compound (1-4390) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 633.

[0793] [Chemical formula]

[0794] Synthesis Example (1-84): Synthesis of Compound (1-3837) Compound (1-3837) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[0795] [Chemical formula]

[0796] Synthesis Example (1-85): Synthesis of Compound (1-4091) Compound (1-4091) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[0797] [Chemical formula]

[0798] Synthesis Example (1-86): Synthesis of Compound (1-3859) Compound (1-3859) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 583.

[0799] [Chemical formula]

[0800] Synthesis Example (1 - 87): Synthesis of Compound (1 - 2416) Compound (1 - 2416) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2019 - 056338. EI-MS: m / z = 583.

[0801] [Chemical Formula]

[0802] Synthesis Example (1 - 88): Synthesis of Compound (1 - 2495) Compound (1 - 2495) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2019 - 056338. EI-MS: m / z = 749.

[0803] [Chemical Formula]

[0804] Synthesis Example (1 - 89): Synthesis of Compound (1 - 2404) Compound (1 - 2404) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2019 - 056338. EI-MS: m / z = 673.

[0805] [Chemical Formula]

[0806] Synthesis Example (1 - 90): Synthesis of Compound (1 - 2440) Compound (1 - 2440) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2019 - 056338. EI-MS: m / z = 965.

[0807] [Chemical Formula]

[0808] Synthesis Example (1-91): Synthesis of Compound (1-2499) Compound (1-2499) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 749.

[0809] [Chemical Formula]

[0810] Synthesis Example (1-92): Synthesis of Compound (1-2413) Compound (1-2413) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 723.

[0811] [Chemical Formula]

[0812] Synthesis Example (1-93): Synthesis of Compound (1-2520) Compound (1-2520) was synthesized by the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 659.

[0813] [Chemical Formula]

[0814] Synthesis Example (1-94): Synthesis of Compound (1-2516) Compound (1-2516) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 839.

[0815] [Chemistry]

[0816] Synthesis Example (1 - 95): Synthesis of Compound (1 - 2519) Compound (1 - 2519) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2010 - 007791. EI - MS: m / z = 749. [Chemistry]

[0817] Synthesis Example (1 - 96): Synthesis of Compound (1 - 2525) Compound (1 - 2525) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2010 - 007791. EI - MS: m / z = 749.

[0818] [Chemistry]

[0819] Synthesis Example (1 - 97): Synthesis of Compound (1 - 2541) Compound (1 - 2541) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 659.

[0820] [Chemistry]

[0821] Synthesis Example (1 - 98): Synthesis of Compound (1 - 2557) Compound (1 - 2557) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 659.

[0822] [Chemistry]

[0823] Synthesis Example (1 - 99): Synthesis of Compound (1 - 2573) Compound (1 - 2573) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 709.

[0824] [Chemical formula]

[0825] Synthesis Example (1 - 100): Synthesis of Compound (1 - 2586) Compound (1 - 2586) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 709.

[0826] [Chemical formula]

[0827] Synthesis Example (1 - 101): Synthesis of Compound (1 - 2594) Compound (1 - 2594) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 709.

[0828] [Chemical formula]

[0829] Synthesis Example (1 - 102): Synthesis of Compound (1 - 2599) Compound (1 - 2599) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 709.

[0830] [Chemical formula]

[0831] Synthesis Example (1 - 103): Synthesis of Compound (1 - 2728) Compound (1 - 2728) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 749.

[0832] [Chemical formula]

[0833] Synthesis Example (1 - 104): Synthesis of Compound (1 - 2579) Compound (1 - 2579) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 889.

[0834] [Chemical formula]

[0835] Synthesis Example (1 - 105): Synthesis of Compound (1 - 2696) Compound (1 - 2696) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 889.

[0836] [Chemical formula]

[0837] Synthesis Example (1 - 106): Synthesis of Compound (1 - 2738) Compound (1 - 2738) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 799.

[0838]

Chem.

[0839] Synthesis Example (1 - 107): Synthesis of Compound (1 - 2743) Compound (1 - 2743) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 799.

[0840]

Chem.

[0841] Synthesis Example (1 - 108): Synthesis of Compound (1 - 2699) Compound (1 - 2699) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 1041.

[0842]

Chem.

[0843] Synthesis Example (1 - 109): Synthesis of Compound (1 - 2603) Compound (1 - 2603) was synthesized by the method described in Korean Patent Publication No. 2018 - 0131963. EI-MS: m / z = 749.

[0844]

Chem.

[0845] Synthesis Example (1 - 110): Synthesis of Compound (1 - 2756) Compound (1-2756) was synthesized by appropriately changing the compounds of the raw materials in the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 925.

[0846]

Chemical formula

[0847] Synthesis Example (1-111): Synthesis of Compound (1-2627) Compound (1-2627) was synthesized by appropriately changing the compounds of the raw materials in the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[0848]

Chemical formula

[0849] Synthesis Example (1-112): Synthesis of Compound (1-2757) Compound (1-2757) was synthesized by appropriately changing the compounds of the raw materials in the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 799.

[0850]

Chemical formula

[0851] Synthesis Example (1-113): Synthesis of Compound (1-2686) Compound (1-2686) was synthesized by appropriately changing the compounds of the raw materials in the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[0852]

Chemical formula

[0853] Synthesis Example (1-114): Synthesis of Compound (1-2615) Compound (1-2615) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[0854]

Chemical formula

[0855] Synthesis Example (1-115): Synthesis of Compound (1-2640) Compound (1-2640) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[0856]

Chemical formula

[0857] Synthesis Example (1-116): Synthesis of Compound (1-2747) Compound (1-2747) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 839.

[0858]

Chemical formula

[0859] Synthesis Example (1-117): Synthesis of Compound (1-2641) Compound (1-2641) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 929.

[0860]

Chemical formula

[0861] Synthesis Example (1-118): Synthesis of Compound (1-2775) Compound (1-2775) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 735.

[0862]

Chemical Structure

[0863] Synthesis Example (1-119): Synthesis of Compound (1-2779) Compound (1-2779) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 735.

[0864]

Chemical Structure

[0865] Synthesis Example (1-120): Synthesis of Compound (1-2787) Compound (1-2787) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 785.

[0866]

Chemical Structure

[0867] Synthesis Example (1-121): Synthesis of Compound (1-2776) Compound (1-2776) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 915.

[0868]

Chemical Structure

[0869] Synthesis Example (1-122): Synthesis of Compound (1-2812) Compound (1-2812) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 825.

[0870] [Chemical formula]

[0871] Synthesis Example (1-123): Synthesis of Compound (1-3914) Compound (1-3914) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 659.

[0872] [Chemical formula]

[0873] Synthesis Example (1-124): Synthesis of Compound (1-3951) Compound (1-3951) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 749.

[0874] [Chemical formula]

[0875] Synthesis Example (1-125): Synthesis of Compound (1-3903) Compound (1-3903) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 659.

[0876] [Chemical formula]

[0877] Synthesis Example (1-126): Synthesis of Compound (1-1335) Compound (1-1335) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[0878]

Chemical Structure

[0879] Synthesis Example (1-127): Synthesis of Compound (1-1337) Compound (1-1337) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[0880]

Chemical Structure

[0881] Synthesis Example (1-128): Synthesis of Compound (1-28) Compound (1-28) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[0882]

Chemical Structure

[0883] Synthesis Example (1-129): Synthesis of Compound (1-275) Compound (1-275) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[0884]

Chemical Structure

[0885] Synthesis Example (1-130): Synthesis of Compound (1-3445) Compound (1-3445) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0886]

Chem.

[0887] Synthesis Example (1-131): Synthesis of Compound (1-3467) Compound (1-3467) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0888]

Chem.

[0889] Synthesis Example (1-132): Synthesis of Compound (1-3434) Compound (1-3434) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0890]

Chem.

[0891] Synthesis Example (1-133): Synthesis of Compound (1-3481) Compound (1-3481) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0892]

Chem.

[0893] Synthesis Example (1-134): Synthesis of Compound (1-3408) Compound (1-3408) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0894] [Chemical Formula]

[0895] Synthesis Example (1-135): Synthesis of Compound (1-3777) Compound (1-3777) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 589.

[0896] [Chemical Formula]

[0897] Synthesis Example (1-136): Synthesis of Compound (1-3594) Compound (1-3594) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[0898] [Chemical Formula]

[0899] Synthesis Example (1-137): Synthesis of Compound (1-3589) Compound (1-3589) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[0900] [Chemical formula]

[0901] Synthesis Example (1-138): Synthesis of Compound (1-3440) Compound (1-3440) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 673.

[0902] [Chemical formula]

[0903] Synthesis Example (1-139): Synthesis of Compound (1-3435) Compound (1-3435) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 753.

[0904] [Chemical formula]

[0905] Synthesis Example (1-140): Synthesis of Compound (1-3572) Compound (1-3572) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 699.

[0906] [Chemical formula]

[0907] Synthesis Example (1-141): Synthesis of Compound (1-3453) Compound (1-3453) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 825.

[0908]

Chem.

[0909] Synthesis Example (1 - 142): Synthesis of Compound (1 - 3562) Compound (1 - 3562) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 623.

[0910]

Chem.

[0911] Synthesis Example (1 - 143): Synthesis of Compound (1 - 3559) Compound (1 - 3559) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 623.

[0912]

Chem.

[0913] Synthesis Example (1 - 144): Synthesis of Compound (1 - 3522) Compound (1 - 3522) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 573.

[0914]

Chem.

[0915] Synthesis Example (1 - 145): Synthesis of Compound (1 - 4014) Compound (1-4014) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 739.

[0916]

Chemical formula

[0917] Synthesis Example (1-146): Synthesis of Compound (1-4018) Compound (1-4018) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0918]

Chemical formula

[0919] Synthesis Example (1-147): Synthesis of Compound (1-3762) Compound (1-3762) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[0920]

Chemical formula

[0921] Synthesis Example (1-148): Synthesis of Compound (1-2912) Compound (1-2912) was synthesized by appropriately modifying the compound of the raw materials in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0922]

Chemical formula

[0923] Synthesis Example (1-149): Synthesis of Compound (1-3284) Compound (1-3284) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0924]

Chemical formula

[0925] Synthesis Example (1-150): Synthesis of Compound (1-3736) Compound (1-3736) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[0926]

Chemical formula

[0927] Synthesis Example (1-151): Synthesis of Compound (1-3770) Compound (1-3770) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 589.

[0928]

Chemical formula

[0929] Synthesis Example (1-152): Synthesis of Compound (1-2873) Compound (1-2873) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 648.

[0930]

Chemical formula

[0931] Synthesis Example (1-153): Synthesis of Compound (1-3249) Compound (1-3249) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[0932]

Chemical Structure

[0933] Synthesis Example (1-154): Synthesis of Compound (1-3296) Compound (1-3296) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[0934]

Chemical Structure

[0935] Synthesis Example (1-155): Synthesis of Compound (1-2917) Compound (1-2917) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 803.

[0936]

Chemical Structure

[0937] Synthesis Example (1-156): Synthesis of Compound (1-3768) Compound (1-3768) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 723.

[0938]

Chemical Structure

[0939] Synthesis Example (1-157): Synthesis of Compound (1-3780) Compound (1-3780) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 789.

[0940] [Chemical Formula]

[0941] Synthesis Example (1-158): Synthesis of Compound (1-3963) Compound (1-3963) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0942] [Chemical Formula]

[0943] Synthesis Example (1-159): Synthesis of Compound (1-4112) Compound (1-4112) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[0944] [Chemical Formula]

[0945] Synthesis Example (1-160): Synthesis of Compound (1-4052) Compound (1-4052) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 699.

[0946] [Chemical Formula]

[0947] Synthesis Example (1-161): Synthesis of Compound (1-4047) Compound (1-4047) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[0948] [Chemical Formula]

[0949] Synthesis Example (1-162): Synthesis of Compound (1-3778) Compound (1-3778) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 748.

[0950] [Chemical Formula]

[0951] Synthesis Example (1-163): Synthesis of Compound (1-4008) Compound (1-4008) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 497.

[0952] [Chemical Formula]

[0953] Synthesis Example (1-164): Synthesis of Compound (1-802) Compound (1-802) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 497.

[0954] [Chemistry]

[0955] Synthesis Example (1 - 165): Synthesis of Compound (1 - 804) Compound (1 - 804) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 513.

[0956] [Chemistry]

[0957] Synthesis Example (1 - 166): Synthesis of Compound (1 - 3784) Compound (1 - 3784) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 547.

[0958] [Chemistry]

[0959] Synthesis Example (1 - 167): Synthesis of Compound (1 - 808) Compound (1 - 808) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 547.

[0960] [Chemistry]

[0961] Synthesis Example (1 - 168): Synthesis of Compound (1 - 801) Compound (1 - 801) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI-MS: m / z = 572.

[0962]

Chem.

[0963] Synthesis Example (1 - 169): Synthesis of Compound (1 - 4142) Compound (1 - 4142) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 713.

[0964]

Chem.

[0965] Synthesis Example (1 - 170): Synthesis of Compound (1 - 4145) Compound (1 - 4145) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 865.

[0966]

Chem.

[0967] Synthesis Example (1 - 171): Synthesis of Compound (1 - 4138) Compound (1 - 4138) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017 - 116885. EI - MS: m / z = 713.

[0968]

Chem.

[0969] Synthesis Example (1 - 172): Synthesis of Compound (1 - 4165) Compound (1-4165) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[0970]

Chem.

[0971] Synthesis Example (1-173): Synthesis of Compound (1-4168) Compound (1-4168) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[0972]

Chem.

[0973] Synthesis Example (1-174): Synthesis of Compound (1-4152) Compound (1-4152) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[0974]

Chem.

[0975] Synthesis Example (1-175): Synthesis of Compound (1-4143) Compound (1-4143) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[0976]

Chem.

[0977] Synthesis Example (1-176): Synthesis of Compound (1-3849) Compound (1-3849) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 863.

[0978]

Chemical Structure

[0979] Synthesis Example (1-177): Synthesis of Compound (1-4434) Compound (1-4434) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 601.

[0980]

Chemical Structure

[0981] Synthesis Example (1-178): Synthesis of Compound (1-4429) Compound (1-4429) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 601.

[0982]

Chemical Structure

[0983] Synthesis Example (1-179): Synthesis of Compound (1-4458) Compound (1-4458) was synthesized by appropriately modifying the starting compounds of the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 665.

[0984]

Chemical Structure

[0985] Synthesis Example (1-180): Synthesis of Compound (1-4409) Compound (1-4409) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[0986] [Chemical formula]

[0987] Synthesis Example (1-181): Synthesis of Compound (1-4404) Compound (1-4404) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[0988] [Chemical formula]

[0989] Synthesis Example (1-182): Synthesis of Compound (1-4427) Compound (1-4427) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 615.

[0990] [Chemical formula]

[0991] Synthesis Example (1-183): Synthesis of Compound (1-2973) Compound (1-2973) was synthesized by appropriately changing the starting compounds in the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 497.

[0992] [Chemical formula]

[0993] Synthesis Example (1-184): Synthesis of Compound (1-4747) Compound (1-4747) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[0994]

Chemical Structure

[0995] Synthesis Example (1-185): Synthesis of Compound (1-3444) Compound (1-3444) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 673.

[0996]

Chemical Structure

[0997] Synthesis Example (1-186): Synthesis of Compound (1-3450) Compound (1-3450) was synthesized by appropriately modifying the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 725.

[0998]

Chemical Structure

[0999] Synthesis Example (1-187): Synthesis of Compound (1-1355) Compound (1-12) (1 g), 5% platinum-carbon (5% Pt / C, 300 mg), heavy water (40 mL), cyclohexane (cHex, 20 mL), and isopropyl alcohol (IPA, 5 mL) were placed in a flask under an argon atmosphere and heated at 100 °C. After the reaction, water and chloroform were added for liquid-liquid extraction. The organic layer was dried over magnesium sulfate and filtered, and then the organic layer was concentrated. The crude product obtained was recrystallized to obtain the target compound (1-1355). EI-MS: m / z = 532.

[1000]

Chemical Structure

[1001] Synthesis Example (1-188): Synthesis of Compound (1-1359) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1359) was synthesized. EI-MS: m / z = 532.

[1002]

Chemical Structure

[1003] Synthesis Example (1-189): Synthesis of Compound (1-1390) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1390) was synthesized. EI-MS: m / z = 668.

[1004]

Chemical Structure

[1005] Synthesis Example (1-190): Synthesis of Compound (1-1496) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1496) was synthesized. EI-MS: m / z = 749.

[1006]

Chemical Structure

[1007] Synthesis Example (1-191): Synthesis of Compound (1-1598) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1598) was synthesized. EI-MS: m / z = 584.

[1008] [Chemical formula]

[1009] Synthesis Example (1-192): Synthesis of Compound (1-1658) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1658) was synthesized. EI-MS: m / z = 584.

[1010] [Chemical formula]

[1011] Synthesis Example (1-193): Synthesis of Compound (1-1789) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1789) was synthesized. EI-MS: m / z = 520.

[1012] [Chemical formula]

[1013] Synthesis Example (1-194): Synthesis of Compound (1-1791) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1791) was synthesized. EI-MS: m / z = 624.

[1014] [Chemical formula]

[1015] Synthesis Example (1-195): Synthesis of Compound (1-1825) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1825) was synthesized. EI-MS: m / z = 572.

[1016] [Chemical formula]

[1017] Synthesis Example (1-196): Synthesis of Compound (1-1468) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1468) was synthesized. EI-MS: m / z = 668.

[1018] [Chemical formula]

[1019] Synthesis Example (1-197): Synthesis of Compound (1-1498) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1498) was synthesized. EI-MS: m / z = 908.

[1020] [Chemical formula]

[1021] Synthesis Example (1-198): Synthesis of Compound (1-2389) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-2389) was synthesized. EI-MS: m / z = 664.

[1022] [Chemical formula]

[1023] Synthesis Example (1-199): Synthesis of Compound (1-1618) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1618) was synthesized. EI-MS: m / z = 768.

[1024]

Chemical formula

[1025] Synthesis Example (1-200): Synthesis of Compound (1-1372) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1372) was synthesized. EI-MS: m / z = 612.

[1026]

Chemical formula

[1027] Synthesis Example (1-201): Synthesis of Compound (1-1615) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1615) was synthesized. EI-MS: m / z = 664.

[1028]

Chemical formula

[1029] Synthesis Example (1-202): Synthesis of Compound (1-1783) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1783) was synthesized. EI-MS: m / z = 704.

[1030]

Chemical formula

[1031] Synthesis Example (1-203): Synthesis of Compound (1-1356) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1356) was synthesized. EI-MS: m / z = 692.

[1032]

Chemical formula

[1033] Synthesis Example (1-204): Synthesis of Compound (1-1626) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1626) was synthesized. EI-MS: m / z = 560.

[1034]

Chemical formula

[1035] Synthesis Example (1-205): Synthesis of Compound (1-1467) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1467) was synthesized. EI-MS: m / z = 508.

[1036]

Chemical formula

[1037] Synthesis Example (1-206): Synthesis of Compound (1-1347) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1347) was synthesized. EI-MS: m / z = 588.

[1038]

Chemical formula

[1039] Synthesis Example (1-207): Synthesis of Compound (1-1860) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1860) was synthesized. EI-MS: m / z = 572.

[1040]

Chemical formula

[1041] Synthesis Example (1-208): Synthesis of Compound (1-1855) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-1855) was synthesized. EI-MS: m / z = 520.

[1042]

Chemical formula

[1043] Synthesis Example (1-209): Synthesis of Compound (1-2397) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-2397) was synthesized. EI-MS: m / z = 560.

[1044]

Chemical formula

[1045] Synthesis Example (1-210): Synthesis of Compound (1-2398) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-2398) was synthesized. EI-MS: m / z = 508.

[1046]

Chemical formula

[1047] Synthesis Example (1-211): Synthesis of Compound (1-4655) Compound (1-4655) was synthesized by appropriately changing the compounds of the raw materials in the method described in the above Synthesis Example (1-56). EI-MS: m / z = 526.

[1048]

Chemical formula

[1049] Synthesis Example (1-212): Synthesis of Compound (1-4660) Compound (1-4660) was synthesized by appropriately changing the compounds of the raw materials in the method described in the above Synthesis Example (1-56). EI-MS: m / z = 592.

[1050]

Chemical formula

[1051] Synthesis Example (1-213): Synthesis of Compound (1-2388) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-2388) was synthesized. EI-MS: m / z = 613.

[1052]

Chemical formula

[1053] Synthesis Example (1-214): Synthesis of Compound (1-4573) Using the same method as in the above-described Synthesis Example (1-187), the compound represented by the formula (1-4573) was synthesized. EI-MS: m / z = 601.

[1054]

Chemical formula

[1055] Synthesis Example (1-215): Synthesis of Compound (1-4579) Compound (1-4579) was synthesized by appropriately changing the raw material compounds in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 588.

[1056]

Chemical formula

[1057] Synthesis Example (1-216): Synthesis of Compound (1-4510) Using the same method as in the aforementioned Synthesis Example (1-187), the compound represented by the formula (1-4510) was synthesized. EI-MS: m / z = 601.

[1058]

Chemical formula

[1059] Synthesis Example (1-217): Synthesis of Compound (1-4701) Using the same method as in the aforementioned Synthesis Example (1-187), the compound represented by the formula (1-4701) was synthesized. EI-MS: m / z = 640.

[1060]

Chemical formula

[1061] Synthesis Example (1-218): Synthesis of Compound (1-4688) Compound (1-4688) was synthesized by appropriately changing the raw material compounds in the method described in the aforementioned Synthesis Example (1-56). EI-MS: m / z = 631.

[1062]

Chemical formula

[1063] Synthesis Example (1-219): Synthesis of Compound (1-4715) Compound (1-4715) was synthesized by appropriately changing the starting compounds of the method described in Synthesis Example (1-56) above. EI-MS: m / z = 624.

[1064]

Chemical Formula

[1065] Synthesis Example (1-220): Synthesis of Compound (1-4565) Using the same method as in Synthesis Example (1-187) described above, the compound represented by formula (1-4565) was synthesized. EI-MS: m / z = 680.

[1066]

Chemical Formula

[1067] Synthesis Example (1-221): Synthesis of Compound (1-4736) Compound (1-4736) was synthesized by appropriately changing the starting compounds of the method described in Synthesis Example (1-56) above. EI-MS: m / z = 498.

[1068]

Chemical Formula

[1069] Synthesis Example (2-1): Synthesis of Compound (2-41)

Chemical Formula

[1070] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (500 MHz, CDCl 3): δ = 1.47 (s, 36H), 2.17 (s, 3H), 5.97 (s, 2H), 6.68 (d, 2H), 7.28 (d, 4H), 7.49 (dd, 2H), 7.67 (d, 4H), 8.97 (d, 2H).

[1071] Synthesis Example (2-2): Synthesis of Compound (2-31)

Chemical Structure

[1072] Compound (2-31) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015 / 102118.

[1073] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (500 MHz, CDCl 3 ): δ = 1.46 (s, 18H), 1.47 (s, 18H), 6.14 (d, 2H), 6.75 (d, 2H), 7.24 (t, 1H), 7.29 (d, 4H), 7.52 (dd, 2H), 7.67 (d, 4H), 8.99 (d, 2H).

[1074] Synthesis Example (2-3): Synthesis of Compound (2-46)

Chemical Structure

[1075] Compound (2-46) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015 / 102118.

[1076] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl 3): δ = 1.20 (s, 9H), 1.37 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 2.18 (s, 3H), 5.97 (s, 1H), 6.08 (d, 1H), 6.63 (d, 1H), 6.66 (d, 1H), 7.20 (d, 2H), 7.27 (d, 2H), 7.32 (dd, 1H), 7.48 (dd, 1H), 7.61 (t, 1H), 7.67 (d, 2H), 8.84 (d, 1H), 8.94 (d, 1H).

[1077] Synthesis Example (2-4): Synthesis of Compound (2-37)

Chemical Structure

[1078] Compound (2-37) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015 / 102118.

[1079] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl 3 ): δ = 1.20 (s, 9H...

Claims

1. An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains an anthracene-based compound represented by the following formula (1) as a host material, and a polycyclic aromatic compound represented by the following formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2) as a dopant material. 【Chemical 1】 (In formula (1), Ar c is an aryl which may be substituted or a heteroaryl which may be substituted, R c is hydrogen, alkyl, or cycloalkyl, and Ar 11 、Ar 12 、Ar 13 、Ar 14 、Ar 15 、Ar 16 、Ar 17 、およびAr 18 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, At least one hydrogen in the compound represented by formula (1) may be substituted with a halogen, cyano, or deuterium.) (In formula (2), Ring A, Ring B, and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted, X 1 and X 2 are each independently >O, >N-R, >C(-R) 2 , >S, or >Se, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the >C(-R) 2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and further, R of the >N-R and / or R of the >C(-R) 2 may be bonded to the A ring, B ring, and / or C ring by a linking group or a single bond, In the compound represented by the formula (2) or its multimer, at least one of the aryl ring and the heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - in the cycloalkane may be substituted with -O-, At least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or a halogen.)

2. The polycyclic aromatic compound represented by formula (2) or the multimer of the polycyclic aromatic compound 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 a multimer of a polycyclic aromatic compound 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). The organic electroluminescent device according to claim 1; [Chemical 2] 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, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、and R 11 may be such that adjacent groups among them are bonded to form an aryl ring or a heteroaryl ring together with an a-ring, a b-ring, or a c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, X X is, independently of one another, >O, >S, >N-R, or >C(-R) 2 wherein R of the >N-R is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted, and further, R of the >C(-R) 2 is, independently of one another, aryl which may be substituted with hydrogen, alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl X 1 and X 2 are each independently >O, >N-R, >C(-R) 2 , >S, or >Se, wherein R of the >N-R is aryl having 6 to 12 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, heteroaryl having 2 to 15 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and R of the >C(-R) 2 is hydrogen, aryl having 6 to 12 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and R of the >N-R and / or R of the >C(-R) 2 may be bonded to the a-ring, b-ring, and / or c-ring by -O-, -S-, -C(-R) 2 -, or a single bond, and R of the -C(-R) 2 - are each independently alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, 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 its multimer, at least one of the aryl ring and the heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - in the cycloalkane may be substituted with -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 a halogen, In the case of a multimer, it is a dimer or trimer 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 compound represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a) or formula (2-b), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-a) or formula (2-b). The organic electroluminescent device according to claim 2.

4. The compound represented by formula (2) is any of the compounds represented by the following formula. The organic electroluminescent device according to claim 3; [Chemical Formula 3] 【Chemical Formula 4】 [Chemical Formula 5] In the above formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium.

5. In formula (1) Ar 11 、Ar 12 、Ar 13 、Ar 14 、Ar 15 、Ar 16 、Ar 17 、and Ar 18 which may be any two of aryl or heteroaryl which may be substituted, and the other six are hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, or alkoxy which may be substituted, the organic electroluminescent device according to any one of claims 1 to 4.

6. The organic electroluminescent device according to claim 5, wherein the anthracene-based compound represented by formula (1) is an anthracene-based compound represented by the following formula (1A), (1B), (1C), (1D), or (1E); 【Chemical Formula 6】 In formula (1A), (1B), (1C), (1D) or (1E), Ar c ’, Ar 11 ’’, Ar 12 ’’’, Ar 13 ’’’’, Ar 14 ’’’’’, Ar 15 ’’’’’’, Ar 17 ’’’’’’’, and Ar 18 ’ are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when both hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Ar c ’, Ar 11 ’, Ar 12 ’, Ar 13 ’, Ar 14 ’, Ar 15 ’, Ar 17 ’, or Ar 18 ’ may be bonded with methyl or t-butyl instead of hydrogen to the carbon atoms on the anthracene ring where they are not bonded, At least one hydrogen in the compound represented by formula (1A), (1B), (1C), (1D) or (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 * indicates that position. In formula (A), Y is -O-, -S- or >N-R 39 wherein R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and at least one hydrogen in the hydrocarbon ring, aryl ring or heteroaryl ring formed by adjacent groups among R 21 ~R 28 may be bonded to each other to form a hydrocarbon ring, aryl ring or heteroaryl ring, and may be substituted with optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano, and R 39 is hydrogen or optionally substituted aryl.

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

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

9. Ar 14 、 Ar 15 is an aryl which may be substituted or a heteroaryl which may be substituted, and Ar 11 、 Ar 12 、 Ar 13 、 Ar 16 、 Ar 17 and Ar 18 are all hydrogen, the organic electroluminescent device according to claim 5.

10. Ar C 、 Ar 14 、 and Ar 15 The organic electroluminescent device according to claim 9, wherein at least one selected from the group consisting of is a group containing an anthracene ring.

11. Ar C 、 Ar 14 、 and Ar 15 The organic electroluminescent element according to claim 9, wherein at least one selected from the group consisting of contains a group represented by the formula (A'); 【Chemical 8】 In formula (A'), R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and among R 21 ~R 28 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 in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano.

12. The organic electroluminescent device according to claim 5, wherein the anthracene-based compound represented by formula (1) is represented by any of the following formulas; 【Chemical Formula 9】 In the formula, X is, independently of each other, aryl optionally substituted with aryl or heteroaryl, or heteroaryl optionally substituted with aryl or heteroaryl, and A is, independently of each other, a single bond, arylene optionally substituted with aryl or heteroaryl, or heteroarylene optionally substituted with aryl or heteroaryl.

13. The organic electroluminescent device according to claim 9, wherein at least one hydrogen in the compound represented by formula (1) is substituted with deuterium.

14. An organic electroluminescent device according to any one of claims 1 to 13, having an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, and 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, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

15. The organic electroluminescent device according to claim 14, 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.

16. A display device including the organic electroluminescent device according to any one of claims 1 to 15.

17. An illumination device including the organic electroluminescent device according to any one of claims 1 to 15.

18. An anthracene-based compound represented by the following formula (1); 【Chemical Formula 10】 In formula (1), Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, R c is hydrogen, alkyl, or cycloalkyl, and Ar 14 and Ar 15 is an optionally substituted aryl or an optionally substituted heteroaryl, Ar 11 , Ar 12 , Ar 13 , Ar 16 , Ar 17 and Ar 18 are all hydrogen, Ar C 、 Ar 14 、 and Ar 15 at least one selected from the group consisting of contains a group represented by the formula (A'), At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium; 【Chemical 11】 In formula (A'), R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and among R 21 ~R 28 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 in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano.

19. An anthracene-based compound represented by the following formula (1Aa); 【Chemical 12】 In formula (1Aa), Ar c ’, Ar 14 ’, and Ar 15 ’ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-14), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenyllyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-14). Here, when all of the hydrogens of the methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Ar c ’, Ar 14 ’, or Ar 15 ’ may be bonded to a carbon atom on the anthracene ring to which they are not bonded with methyl or t-butyl instead of hydrogen, The groups represented by formula (A-1) to formula (A-14) are groups obtained by removing one hydrogen at any position of each of formula (A-1) to formula (A-14), and * indicates that position, In Formulae (A-1) to (A-14), Y is -O-, -S-, or >N-R 39 wherein R 39 is hydrogen or aryl, and at least one hydrogen in the group represented by Formulae (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano, provided that at least one hydrogen in the compound represented by formula (1Aa) may be substituted with halogen, cyano, or deuterium, and at least one hydrogen in the compound represented by formula (1Aa) is substituted with deuterium.

20. Ar c' 、 Ar 14 ’ and Ar 15 ’ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of formulas (A-1) to (A-4), and at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of formulas (A-1) to (A-4). The anthracene-based compound according to claim 19.

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

22. The anthracene compound according to claim 19, represented by any of the following formulas. 【Chemical 13】 【Chemical 14】 【Chemical 15】 【Chemical 16】 (In the above formula, D represents deuterium.)

23. An anthracene compound represented by the following formula (1); 【Chemical 17】 In formula (1), Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, R c is hydrogen, alkyl, or cycloalkyl, and Ar 14 、Ar 15 is an aryl which may be substituted or a heteroaryl which may be substituted, Ar 11 、Ar 12 、Ar 13 、Ar 16 、Ar 17 and Ar 18 are all hydrogen, However, Ar C , Ar 14 , and at least one selected from the group consisting of Ar 15 is a group containing an anthracene ring, At least one hydrogen in the compound represented by formula (1) may be substituted with a halogen, cyano, or deuterium.

24. The anthracene compound according to claim 23, wherein the anthracene compound represented by formula (1) is represented by any of the following formulas; 【Chemical Formula 18】 In the formula, X is, independently of each other, an aryl optionally substituted with an aryl or heteroaryl, or a heteroaryl optionally substituted with an aryl or heteroaryl, and A is, independently of each other, a single bond, an arylene optionally substituted with an aryl or heteroaryl, or a heteroarylene optionally substituted with an aryl or heteroaryl.

25. An anthracene compound represented by any of the following formulas. 【Chemical 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemical 24】 【Chemical 25】 (In the above formula, D represents deuterium.)

26. The anthracene compound according to claim 23, represented by any of the following formulas. 【Chemical 26】 【Chemical 27】 【Chemical formula 28】 【Chemical 29】

27. An anthracene compound represented by any of the following formulas. 【Chemical 30】 【Chemical 31】 【Chemical 32】 【Chemical 33】 (In the above formula, D represents deuterium.)

28. An anthracene compound represented by any of the following formulas. 【Chemical 34】 【Chemical 35】 (In the above formula, D represents deuterium.)

29. An anthracene compound represented by any of the following formulas. 【Chemical 36】 (In the above formula, Me represents methyl, tBu represents t-butyl, and CyHex represents cyclohexyl.)

30. An anthracene compound represented by any of the following formulas. 【Chemical 37】 【Chemical Formula 38】 (In the above formula, D represents deuterium.)

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