Organic electroluminescent element and anthracene compound

Abstract

To provide an organic EL element having high external quantum efficiency.SOLUTION: The organic electroluminescent element includes: a pair of electrodes including an anode and a cathode; an emission layer disposed between the pair of electrodes, the emission layer including a specific anthracene compound as a host material and including one of a specific polycyclic aromatic compound and a polymer thereof as a dopant material.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thinner and more energy-efficient, and organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") made from organic materials have been actively studied because they can be easily made lighter and larger. In particular, the development of organic materials with luminescent properties such as blue, one of the three primary colors of light, and the combination of multiple materials that will produce optimal luminescent properties have been actively researched, regardless of whether they are polymeric or low-molecular-weight compounds.

[0003] An organic EL device has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing organic compounds disposed between the pair of electrodes. The layers containing organic compounds include a light-emitting layer and 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 anthracene-based compounds as light-emitting materials for organic electroluminescent devices. In recent years, polycyclic aromatic compounds in which multiple aromatic rings are condensed with a central atom such as boron have been reported as materials for organic electroluminescent devices (Patent Document 2). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2006 / 003842 [Patent Document 2] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, various materials have been developed for use in organic EL devices. However, in order to increase the options for materials for organic EL devices, it is desirable to develop materials made of compounds different from conventional ones. An object of the present invention is to provide an organic EL device using a new combination of materials. An object of the present invention is to provide an organic EL device having high external quantum efficiency. [Means for solving the problem]

[0007] As a result of intensive investigations aimed at solving the above-mentioned problems, the present inventors have found that an excellent organic EL device can be obtained by using an emitting layer containing a specific anthracene-based compound as a host material and a polycyclic aromatic compound having multiple fused aromatic rings as a dopant material, and have completed the present invention. That is, the present invention provides the following organic electroluminescent device and an anthracene-based compound.

[0008] <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, as a host material, an anthracene-based compound represented by the following formula (1), and, as a dopant material, a polycyclic aromatic compound represented by the following formula (2) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2):

[0009] [ka]

[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 atom 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 atom in these rings may be substituted; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >S, or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the >NR and / or R of the >C(-R)2 may be bonded to the A ring, the B ring, and / or the C ring via a linking group or a single bond, In the compound represented by formula (2) or a multimer thereof, at least one of the aryl ring and the heteroaryl ring may be fused with at least one cycloalkane, at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or halogen.

[0012] <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 the 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); <1> the organic electroluminescent device according to the present invention;

[0013] [ka]

[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 11are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with an 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 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (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 atom in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; X X are each independently >O, >S, >NR, or >C(—R)2, and R of the >NR 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 each independently hydrogen, an aryl optionally substituted with alkyl or cycloalkyl, a heteroaryl optionally substituted with alkyl or cycloalkyl, an alkyl, or a cycloalkyl; X 1 and X 2are each independently >O, >NR, >C(-R)2, >S, or >Se, and R of the >NR 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 of the >C(-R)2 is hydrogen, an aryl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. R of said >NR and / or R of said >C(-R)2 may be bonded to said ring a, ring b, and / or ring c via -O-, -S-, -C(-R)2-, or a single bond, and each R of said -C(-R)2- is 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 a multimer thereof, at least one of the aryl ring and the heteroaryl ring may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom 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 polymer, 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 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). <2> The organic electroluminescent device according to claim 1.

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

[0017] [ka]

[0018] [ka] In the above formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium.

[0019] <5> In equation (1), Ar 11 , Ar 12 , Ar 13 , Ar 14 , Ar 15 , Ar 16 , Ar 17 , and Ar 18 any two of the above are 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; <1> ~ <4> 10. The organic electroluminescent device according to claim 9, wherein

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

[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 each independently represents phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), in which at least one hydrogen atom 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), in which when two hydrogen atoms of methylene in fluorenyl and benzofluorenyl are both 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 A carbon atom on the anthracene ring to which ' is not bonded may have a methyl or t-butyl bonded instead of a hydrogen atom, At least one hydrogen atom in the compound represented by formula (1A), (1B), (1C), (1D) or (1E) may be substituted with a halogen atom, a cyano atom or a deuterium atom; The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position, In formula (A), Y is —O—, —S—, or >NR 39 and 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; R 21 ~R 28 adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen atom 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; 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 formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any position in each of formulae (A-1) to (A-14), and * indicates the position; In formulas (A-1) to (A-14), Y is —O—, —S—, or >NR 39 and R 39represents hydrogen or aryl, and at least one hydrogen atom in the groups 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. <6> The organic electroluminescent device according to claim 1.

[0023] [ka]

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

[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 all hydrogen, <5> The organic electroluminescent device according to claim 1. <10> Ar C , Ar 14 , and Ar 15 wherein at least one selected from the group consisting of is a group containing an anthracene ring. <9> The organic electroluminescent device according to claim 1.

[0026] <11> Ar C , Ar 14 , and Ar 15 At least one selected from the group consisting of: <9> the organic electroluminescent device according to the present invention; [ka]

[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; R 21 ~R 28Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, and at least one hydrogen atom 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.

[0028] <12> At least one hydrogen atom in the compound represented by formula (1) is replaced with a deuterium atom. <9> The organic electroluminescent device according to claim 1. <13> an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein 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, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives; <1> ~ <12> 10. The organic electroluminescent device according to claim 9, wherein

[0029] <14> 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, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes; <13> The organic electroluminescent device according to claim 1. <15> <1> ~ <14> A display device comprising the organic electroluminescent element according to any one of the above items. <16> <1> ~ <14> 10. A lighting device comprising the organic electroluminescent element according to any one of claims 1 to 9.

[0030] <17> An anthracene-based compound represented by the following formula (1): [ka]

[0031] In formula (1), Ar c is an optionally substituted aryl or an 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 atom in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

[0032] <18> Represented by the following formula (1Aa) <17> an anthracene-based compound according to [ka]

[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 one of formulas (A-1) to (A-14), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-14), and when hydrogen atoms of methylene groups in fluorenyl and benzofluorenyl are both substituted with phenyl, these phenyls may be bonded to each other via a single bond, and Ar c ', Ar 14 ', or Ar 15 A carbon atom on the anthracene ring to which ' is not bonded may have a methyl or t-butyl bonded instead of a hydrogen atom, At least one hydrogen atom in the compound represented by formula (1Aa) may be substituted with a halogen atom, a cyano atom, or a deuterium atom; The groups represented by formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any position in each of formulae (A-1) to (A-14), and * indicates the position; In formulas (A-1) to (A-14), Y is —O—, —S—, or >NR 39 and R 39 represents hydrogen or aryl, and at least one hydrogen atom in the groups 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; However, 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.

[0034] <19> Ar c’ , Ar 14 ' and Ar 15 each independently represents 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 atom 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); <18> The anthracene compound according to claim 1. <20> In formula (1Aa), at least hydrogen bonded to the 10-position of the anthracene ring is substituted with deuterium. <18> or <19> The anthracene compound according to claim 1.

[0035] <21> Represented by one of the following formulas <18> The anthracene compound according to claim 1. [ka]

[0036] [ka]

[0037] [ka]

[0038] [ka] (In the above formula, D represents deuterium.)

[0039] <22> Represented by one of the following formulas <17> The anthracene compound according to claim 1. [ka]

[0040] [ka]

[0041] [ka] [ka]

[0042] [ka]

[0043] [ka]

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

[0045] <23> Represented by one of the following formulas <17> The anthracene compound according to claim 1. [ka]

[0046] [ka]

[0047] [ka]

[0048] [ka]

[0049] <24> Represented by one of the following formulas <17> The anthracene compound according to claim 1. [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka] (In the above formula, D represents deuterium.)

[0053] <25> Represented by one of the following formulas <17> The anthracene compound according to claim 1. [ka]

[0054] [ka] (In the above formula, D represents deuterium.)

[0055] <26> Represented by one of the following formulas <17> The anthracene compound according to claim 1. [ka] (In the above formula, Me represents methyl, tBu represents t-butyl, and CyHex represents cyclohexyl.)

[0056] <27> Represented by one of the following formulas <17> The anthracene compound according to claim 1. [ka]

[0057] [ka] (In the above formula, D represents deuterium.) [Effects 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 high external quantum efficiency and is capable of emitting light at a low voltage. The present invention also provides an anthracene-based compound that can be used in the production of the organic EL device. [Brief explanation of the drawings]

[0059] [Figure 1] 1 is a schematic cross-sectional view showing an example of an organic EL element of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0060] The present invention will be described in detail below. The following explanation of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" means a range that includes the numerical values before and after "to" as the lower and upper limits. In addition, in this specification, "hydrogen" in the explanation of structural formulas means "hydrogen atom (H)."

[0061] In this specification, chemical structures and substituents are sometimes represented by the number of carbon atoms. However, when a chemical structure is substituted with a substituent or when a substituent is further substituted with a substituent, the number of carbon atoms refers to the number of carbon atoms in each of the chemical structure and the substituent, and does not refer to the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X," and the carbon number Y is not the total number of carbon atoms in substituents A and B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (with no carbon number restriction)," and the carbon number Y is not the total number of carbon atoms in substituents A and B.

[0062] <<Organic electroluminescent device>> The organic electroluminescent device of the present invention has a pair of electrodes consisting 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 device of the present invention.

[0063] The organic EL device 100 shown in FIG. 1 includes 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, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the 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] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0065] Not all of the above layers are essential, and the minimum structural unit is a configuration consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be optionally provided. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0066] The layers constituting the organic EL element may be configured as follows: "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" as described above, as well 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 ... transport The configuration may be, for example, "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 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," or "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0067] 1. Light-emitting layer in organic electroluminescent devices 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. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited to emit light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film and that exhibits strong luminescence (fluorescence) efficiency in a solid state.

[0068] There are two main emission mechanisms for organic EL elements: fluorescence, which uses light emitted from an excited singlet state, and phosphorescence, which uses light emitted from an excited triplet state. Common fluorescent materials have a low exciton utilization efficiency of 25% at most. However, by using a phenomenon known as triplet-triplet fusion (TTF), in which a singlet exciton is generated from multiple triplet excitons, up to 40-62.5% of the energy can be utilized for emission.

[0069] Singlet excitons can be generated from triplet excitons in two ways: on the host material molecules or on the dopant material molecules. In this case, the triplet energy level of the dopant material is preferably higher than that of the host material. When this triplet energy level relationship is satisfied, triplet excitons generated on the host material do not transfer to the dopant material with a higher triplet energy. Furthermore, triplet excitons generated on the dopant material molecules rapidly transfer energy to the host material molecules. That is, triplet excitons from the host material efficiently collide with each other on the host material, generating singlet excitons without transferring to the dopant material. Furthermore, when the singlet energy level of the dopant material is lower than that of the host material, singlet excitons generated by the TTF phenomenon rapidly transfer energy from the host material to the dopant material, contributing to the fluorescent emission of the dopant material. Furthermore, the energy transfer from the host to the dopant in this case is Förster energy transfer. In general, it is known that in organic EL devices, highly efficient Förster energy transfer occurs when the overlap integral between the host's fluorescence spectrum and the dopant's absorption spectrum is large and the host and dopant are in close proximity and appropriately oriented.

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

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

[0072] 1-1-1.Anthracene compounds The anthracene 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). [ka]

[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 18are 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, and at least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

[0074] The "aryl" in the "optionally substituted aryl" in formula (1) includes, for example, 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 monocyclic phenyl, bicyclic bicyclic biphenylyl, fused bicyclic naphthyl, tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), fused tricyclic anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, fused tetracyclic triphenylenyl, pyrenyl, naphthacenyl, benzofluorenyl, and fused pentacyclic perylenyl and pentacenyl. In this specification, the term "fluorenyl" refers to fluorenyl or fluorenyl in which one or two of the two hydrogen atoms on the methylene are substituted with methyl. In addition, the term "benzofluorenyl" refers to benzofluorenyl or benzofluorenyl in which one or two of the two hydrogen atoms on the methylene are substituted with methyl.

[0076] Examples of the "heteroaryl" in the "optionally substituted heteroaryl" in formula (1) 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. Examples of heteroaryls include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0077] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cyclohex ... Examples thereof include benzoyl, quinazolyl, 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, and naphthobenzothienyl.

[0078] As the aryl and heteroaryl in each of the "optionally substituted diarylamino," "optionally substituted diheteroarylamino," and "optionally substituted arylheteroarylamino" in formula (1), those described above as the "aryl" and "heteroaryl" can be cited.

[0079] Specific examples include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0080] The "alkyl" in "alkyl" and "optionally substituted alkyl" in formula (1) 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 even 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, Examples include 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, and n-eicosyl.

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

[0083] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as 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, and decahydroazulenyl.

[0084] The "alkenyl" in the "optionally substituted alkenyl" in formula (1) includes a linear alkenyl having 2 to 24 carbon atoms and a branched alkenyl having 4 to 24 carbon atoms. An alkenyl having 2 to 18 carbon atoms is preferred, an alkenyl having 2 to 12 carbon atoms is more preferred, an alkenyl having 2 to 6 carbon atoms is even more preferred, and an alkenyl having 2 to 4 carbon atoms is particularly preferred. Specific examples of "alkenyl" include vinyl, allyl, butadienyl, and the like.

[0085] Examples of the "alkoxy" in the "optionally substituted alkoxy" in formula (1) include straight-chain alkoxy having 1 to 24 carbon atoms and branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 4 carbon atoms (branched-chain alkoxy having 3 to 4 carbon atoms) is particularly preferred.

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

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

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

[0089] The "optionally substituted silyl" in formula (1) includes trialkylsilyl. The "trialkylsilyl" includes silyl in which three hydrogen atoms are independently substituted with alkyl, and this alkyl is the same as the above-mentioned Ar 4 and those explained as "alkyl" for X. Preferred alkyl for substitution is alkyl having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, cyclobutyl, etc.

[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, and t-butyldi-i-propylsilyl.

[0091] Ar in formula (1) c , Ar 11 , Ar 12 , Ar 13 , Ar 14 , Ar 15 , Ar 16 , Ar 17 , and Ar 18 When the term "optionally substituted" is used, examples of the substituent include alkyl, aryl, and heteroaryl. Examples of the alkyl, aryl, and heteroaryl include those mentioned above for "alkyl," "aryl," and "heteroaryl." The number of substituents may be any number up to the maximum number of possible substitutions, and is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1. When there are multiple substituents, the multiple substituents may be bonded to each other. For example, when both hydrogen atoms of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond.

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

[0093] [ka]

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

[0095] In formulas (1-X4) to (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 formulas (1-X1) to (1-X7), Ar 21 , Ar 22 , Ar 23 , Ar 24 , Ar 25 , Ar 26 , Ar 27 and Ar 28 is an anthracenyl, at least one hydrogen atom in the anthracenyl may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) described below.

[0097] In addition, any one or more hydrogen atoms in each of the groups represented by formulae (1-X1) to (1-X7) may be substituted with 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 groups represented by formula (A) described below.

[0099] The "optionally substituted heteroaryl" also includes a group represented by any one of formulas (A), (B), (C), (D) and (E) described below.

[0100] Furthermore, preferred examples of the "optionally substituted aryl" or "optionally substituted heteroaryl" include groups in which an aryl or heteroaryl is bonded to the carbon atom adjacent to the carbon atom at which the group is bonded. Specifically, these are groups represented by the following formula (1-XB), and the group represented by formula (1-X6) is an example of the group represented by formula (1-XB).

[0101] [ka]

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

[0103] For example, 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 all hydrogen, and Ar C , Ar 14 and Ar 15 In one preferred embodiment, an anthracene compound has at least one group selected from the group consisting of the following: c is preferably hydrogen.

[0104] Specific examples include compounds represented by the following formula numbers in Table 1: (1-124), (1-4133), (1-148), (1-150), (1-136), (1-4155), (1-3268), (1-4114), (1-4121), (1-4119), (1-4120), (1-4107), (1-43 17), (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), (1-4 198), (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 compound represented by formula (1) also preferably has a substituent containing an anthracene ring as the "optionally substituted aryl" or "optionally substituted heteroaryl". For example, 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 When both are hydrogen, Ar C , Ar 14 , and Ar 15 It is also preferable that at least one selected from the group consisting of is a group containing an anthracene ring. c is preferably hydrogen.

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

[0107] [ka]

[0108] In each of the above formulas, 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 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, the aryl and heteroaryl are the same as those in Ar of formula (1). c The descriptions of aryl and heteroaryl in, for example, E.g., can be referred to.

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

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

[0111] Specific examples include compounds represented by the following formula numbers in Table 1: (1-2495), (1-2404), (1-2440), (1-2499), (1-2413), (1-2516), (1-2519), (1-2525), (1-2541), (1-2557), (1-2573), (1-2586), (1-2694), (1-2599), (1-2728), (1-2579), (1-2696), (1-2738), (1-274 3), (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] Other specific examples of "optionally substituted aryl" and "optionally substituted heteroaryl" include the substituents represented by the structural formulas described below as explanations of the symbols in Table 1.

[0113] At least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen atom, cyano atom, or deuterium atom. In this case, "halogen" includes fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogen atoms in the compound represented by formula (1) are substituted with deuterium atoms 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 R are hydrogen atoms, a compound in which at least one hydrogen atom is substituted with a deuterium atom is preferred. In this case, the substitution position of the deuterium atom is not limited. For example, at least Rc Compounds where is deuterium, Ar c and Ar 11 ~Ar 18 Examples of the compound include a compound in which at least one hydrogen atom in at least one compound selected from the group consisting of: is substituted with deuterium, or a compound in which all hydrogen atoms 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 Ar 11 , Ar 12 , Ar 13 , Ar 16 , Ar 17 and Ar 18 When both are hydrogen, R c Preferred examples of anthracene compounds are those in which R is alkyl or cycloalkyl. Specific examples include the compounds represented by the following formula numbers in Table 1: (1-4434), (1-4429), (1-4458), (1-4409), (1-4404), and (1-4427).

[0117] In formula (1), Ar 11 ~Ar 18 It is preferable that at least two of the substituents be an optionally substituted aryl or an 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 an optionally substituted aryl and an optionally substituted heteroaryl are bonded to the anthracene ring.

[0118] The anthracene compound represented by formula (1) is Ar 11 ~Ar 18It is more preferred that two of the groups are 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. That is, it is more preferred that the anthracene compound represented by formula (1) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0119] The anthracene compound represented by formula (1) is Ar 11 ~Ar 18 It is more preferred that any two of Ar are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl. 11 ~Ar 18 any two of which are optionally substituted aryl or optionally substituted heteroaryl, and R c is hydrogen and Ar 11 ~Ar 18 It is particularly preferred that the other six are hydrogen.

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

[0121] In 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 18Each of the ' is independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) described below, and at least one hydrogen atom 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) described below. Here, when both hydrogen atoms of the methylenes in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 The carbon atoms of the anthracene ring to which ' is not attached may have methyl or t-butyl attached instead of hydrogen.

[0122] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 When each of "1" and "2" is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferably a group represented by any one of the above formulas (1-X1) to (1-X7).

[0123] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18It is more preferable that each of the ' groups independently represent phenyl, biphenylyl (particularly biphenyl-2-yl or biphenyl-4-yl), terphenylyl (particularly m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or a group represented by any one of formulas (A-1) to (A-4) described below, in which case at least one hydrogen atom in these groups may be substituted by phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of formulas (A-1) to (A-4) described below.

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

[0125] The group represented by the above formula (A) will be explained below. [ka]

[0126] In formula (A), Y is —O—, —S—, or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 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; R 21 ~R 28Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, and at least one hydrogen atom 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 atom, a hydroxyl group, or a cyano group. The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position.

[0127] R in formula (A) 21 ~R 28 Among these, it is preferred that all of them are hydrogen, or at least one of them is an aryl which may be substituted or an heteroaryl which may be substituted, more preferred that all of them are hydrogen, or at least one of them is an aryl which may be substituted or an heteroaryl which may be substituted, and the others are hydrogen, and even more preferred that all of them are hydrogen, or one or two of them is an aryl which may be substituted or an heteroaryl which may be substituted, and the others are hydrogen. 21 ~R 28 When adjacent groups among these are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, hydrogen atoms in the formed ring are not replaced by substituents, and the remaining R 21 ~R 28 is hydrogen, or a substituent replacing a hydrogen in the formed ring and the remaining R 21 ~R 28 Preferably, at least one of R is an optionally substituted aryl or an optionally substituted heteroaryl, and hydrogen atoms in the formed ring are not replaced by a substituent, and the remaining R 21 ~R28 is hydrogen, or a substituent replacing a hydrogen in the formed ring and the remaining R 21 ~R 28 It is more preferred that one or two of these are optionally substituted aryl or optionally substituted heteroaryl.

[0128] R in formula (A) 21 ~R 28 The "alkyl" in the "optionally substituted alkyl" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0129] 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, Examples include 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, and n-eicosyl.

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

[0131] Specific examples of "aryl" include phenyl, which is a monocyclic ring system; biphenylyl, which is a bicyclic ring system; naphthyl, which is a fused bicyclic ring system; terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), which is a tricyclic ring system; anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are fused tricyclic ring systems; triphenylenyl, pyrenyl, naphthacenyl, benzofluorenyl, which are fused tetracyclic ring systems; perylenyl, pentacenyl, etc.

[0132] R in formula (A) 21 ~R 28 Examples of the "heteroaryl" in the "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 include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0133] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, and isoxazolyl. Examples include noryl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuranyl, and naphthobenzothienyl.

[0134] R in formula (A) 21 ~R 28 Examples of the "alkoxy" in "optionally substituted alkoxy" include straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 4 carbon atoms (branched-chain alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0135] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[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 one of the above-mentioned R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[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 one of the above-mentioned R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0138] R in formula (A) 21 ~R 28 The "trialkylsilyl" in the above formula is a group in which three hydrogen atoms in the silyl are each independently substituted with an alkyl, and this alkyl is the same as the above-mentioned R 21 ~R 28 Examples of the alkyl group include those described as "alkyl" in the above. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, n-butyl, s-butyl, t-butyl, and cyclobutyl.

[0139] Specific examples of the "trialkylsilyl" 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, and t-butyldi-i-propylsilyl.

[0140] R in formula (A) 21 ~R 28 The "substituted amino" in the "optionally substituted amino" includes, for example, amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl atoms is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl atoms is a diheteroaryl-substituted amino, and an amino in which two hydrogen atoms are substituted with an aryl and a heteroaryl atom is an arylheteroaryl-substituted amino. The aryl and heteroaryl atoms are substituted with the R 21 ~R 28 The groups described as "aryl" and "heteroaryl" in the above can be cited.

[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 The "halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0143] R in formula (A) 21 ~R 28 Some of the groups described as may be substituted as described above, and in this case, the substituents include alkyl, aryl, or heteroaryl. The alkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 The groups described above as "alkyl," "aryl," or "heteroaryl" can be cited.

[0144] "NR" as Y in formula (A) 39 "R" 39 is hydrogen or an optionally substituted aryl, and the aryl is the same as R 21 ~R 28 The groups described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described as substituents for the following can be cited.

[0145] R in formula (A) 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. When no ring is formed, it is a group represented by the following formula (A-1), and when a ring is formed, it is, for example, a group represented by the following formulas (A-2) to (A-14). At least one hydrogen atom 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 may be substituted with the above-mentioned R. 21 ~R 28 The groups described as each group in the above formula can be cited.

[0146] Examples of rings formed by bonding adjacent groups to each other include hydrocarbon rings such as cyclohexane rings, and aryl and heteroaryl rings such as those described above for R 21 ~R 28 These rings are formed so as to be fused 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), of which a group represented by any of formulas (A-1) to (A-11) is preferred, a group represented by any of formulas (A-1) to (A-4) is more preferred, a group represented by any of formulas (A-1), (A-3) and (A-4) is even more preferred, and a group represented by formula (A-1) is most preferred.

[0148] [ka]

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

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

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

[0152] Compounds containing a group represented by formula (A) (particularly a group represented by formula (A) in which Y is -O-) are given as preferred examples of anthracene-based compounds represented by formula (1), and in addition to the compounds already described, the following anthracene-based compounds (a) or (b) are also preferred.

[0153] (a) In formula (1), 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 all hydrogen, and Ar C , Ar 14 and Ar 15 At least one selected from the group consisting of is a group represented by formula (A), and R in formula (A) 21 ~R 28 and Y is >NR 39 If R 39 An anthracene-based compound in which at least one selected from the group consisting of R is aryl or heteroaryl. c is preferably hydrogen.

[0154] Specific examples include compounds represented by the following formula numbers in Table 1: (1-3445), (1-3467), (1-3434), (1-3481), (1-3408), (1-3777), (1-3594), (1-3589), (1-3440), (1-3435), (1-3572), (1-3453), (1-3562), (1-3559), (1-3522), (1-4014), (1-4018), (1-3762), (1-4145), (1-4573), (1-4579), (1-3444), (1-3450), and (1-4747).

[0155] (b) In formula (1), 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 all hydrogen, and Ar C , Ar 14 and Ar 15 An anthracene-based compound in which at least one selected from the group consisting of R is an aryl having a group represented by formula (A) as a substituent or a heteroaryl having a group represented by formula (A) as a substituent. c is preferably hydrogen. Examples of aryl having a group represented by formula (A) as a substituent include groups represented by any of formulas (1-X1) to (1-X6), in which 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), and (1-4510).

[0157] The group represented by the formula (B), the group represented by the formula (C), the group represented by the formula (D), and the group represented by the formula (E) will be explained below. The explanation of each substituent below will be made in accordance with the R 21 ~R 28 You can refer to the explanation in

[0158] [ka]

[0159] In formula (B), Y is —O—, —S— or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 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; R 29 ~R 38 Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. Furthermore, at least one hydrogen atom 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 atom, a hydroxyl group, or a cyano group. The group represented by formula (B) is obtained by removing one hydrogen atom from any position of formula (B), and * indicates the position.

[0160] In formula (B), Y is preferably —O—. R in formula (B) 29 ~R 38Among these, it is preferred that all of them are hydrogen, or at least one of them is an aryl which may be substituted or an heteroaryl which may be substituted, more preferred that all of them are hydrogen, or at least one of them is an aryl which may be substituted or an heteroaryl which may be substituted, and the others are hydrogen, and even more preferred that all of them are hydrogen, or one or two of them is an aryl which may be substituted or an heteroaryl which may be substituted, and the others are hydrogen. 29 ~R 38 When adjacent groups among these are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, hydrogen atoms in the formed ring are not replaced by substituents, and the remaining R 29 ~R 38 is hydrogen, or a substituent replacing a hydrogen in the formed ring and the remaining R 29 ~R 38 Preferably, at least one of R is an optionally substituted aryl or an optionally substituted heteroaryl, and hydrogen atoms in the formed ring are not replaced by a substituent, and the remaining R 29 ~R 38 is hydrogen, or a substituent replacing a hydrogen in the formed ring and the remaining R 29 ~R 38 It is more preferred that one or two of these are optionally substituted aryl or optionally substituted heteroaryl.

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

[0162] [ka]

[0163] More specifically, examples of the group represented by formula (B) include groups represented by the following formulas: In the formula, Y and * are defined as above, and Y is preferably -O-.

[0164] [ka]

[0165] In formula (C), Y is —O—, —S—, or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 41 ~R 48 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; R 41 ~R 48 Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, and at least one hydrogen atom 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 atom, a hydroxyl group, or a cyano group.

[0166] The group represented by formula (C) is a group obtained by removing one hydrogen atom from any position of formula (C), and * indicates the position. In formula (C), Y is >NR 39 When R 39 is preferably an optionally substituted phenyl, and more preferably an unsubstituted phenyl. 39Optionally substituted phenyl is R 42 , R 43 , R 46 , or R 47 may be bonded to the benzene ring as a bond. At least one of Y is preferably -O-, and both Ys are -O-, or one of Ys is -O- and the other is >NR 39 It is more preferable that R 41 ~R 48 are preferably all hydrogen.

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

[0168] [ka]

[0169] More specifically, examples of the group represented by formula (C) include groups represented by the following formulas: In the formula, Y and * are defined as above, and Y is preferably -O-.

[0170] [ka]

[0171] In formula (D), Y is —O—, —S—, or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 51 ~R 58 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; R51 ~R 58 Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, and at least one hydrogen atom 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 atom, a hydroxyl group, or a cyano group.

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

[0173] In formula (E), Y is —O—, —S—, or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 61 ~R 71 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; R 61 ~R 71Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, and at least one hydrogen atom 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 atom, a hydroxyl group, or a cyano group.

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

[0175] Particularly preferred anthracene compounds represented by formula (1) include anthracene compounds represented by the following formula (1Aa). [ka]

[0176] In formula (1Aa), Ar c ', Ar 14', and Ar 15 Each of the ' is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the above formulas (A-1) to (A-11), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the formulas (A-1) to (A-11). When both hydrogen atoms of the methylenes in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. In addition, Ar c ', Ar 14 ', and Ar 15 A carbon atom on the anthracene ring to which "'" is not bonded may be substituted with methyl or t-butyl in place of hydrogen. At least one hydrogen in the compound represented by formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (1Aa) is substituted with deuterium.

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

[0178] In the compound represented by formula (1Aa), at least the carbon atom at the 10-position of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon atom (the carbon atom to which Ar′ is bonded is the 9th position) is substituted with deuterium. That is, the compound represented by formula (1Aa) is preferably a compound represented by the following formula (1Ab). In formula (1Ab), D is deuterium, and Ar c ', Ar 14 ', and Ar 15 "'" has the same definition as in formula (1Aa). D in formula (1Ab) indicates that at least this position is deuterium, and any one or more other hydrogen atoms in formula (1Aa) may also be deuterium, and it is also preferred that all hydrogen atoms in formula (1Aa) are deuterium.

[0179] [ka]

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

[0181] [Table 1] TIFF2025122107000051.tif225170TIFF2025122107000052.tif226170TIFF2025122107000053.tif225170TIFF2025122107000054.tif225170TIFF2025122107000055.tif226170TIFF2025122107000056.tif226170TIFF2025122107000057.tif228170TIFF2025122107000058.tif228170TIFF2025122107000059.tif228170TIFF2025122107000060.tif228170TIFF2025122107000061.tif226170TIFF2025122107000062.tif226170TIFF2025122107000063.tif226170TIFF2025122107000064.tif226170TIFF2025122107000065.tif225170TIFF2025122107000066.tif225170TIFF2025122107000067.tif225170TIFF2025122107000068.tif225170TIFF2025122107000069.tif226170TIFF2025122107000070.tif225170TIFF2025122107000071.tif226170TIFF2025122107000072.tif226170TIFF2025122107000073.tif225170TIFF2025122107000074.tif226170TIFF2025122107000075.tif225170TIFF2025122107000076.tif225170TIFF2025122107000077.tif225170TIFF2025122107000078.tif226170TIFF2025122107000079.tif226170TIFF2025122107000080.tif225170TIFF2025122107000081.tif225170TIFF2025122107000082.tif226170TIFF2025122107000083.tif226170TIFF2025122107000084.tif225170TIFF2025122107000085.tif225170TIFF2025122107000086.tif225170TIFF2025122107000087.tif225170TIFF2025122107000088.tif226170TIFF2025122107000089.tif225170TIFF2025122107000090.tif225170TIFF2025122107000091.tif226170TIFF2025122107000092.tif226170TIFF2025122107000093.tif225170TIFF2025122107000094.tif226170TIFF2025122107000095.tif225170TIFF2025122107000096.tif225170TIFF2025122107000097.tif228170TIFF2025122107000098.tif225170TIFF2025122107000099.tif225170TIFF2025122107000100.tif225170TIFF2025122107000101.tif226170TIFF2025122107000102.tif225170TIFF2025122107000103.tif225170TIFF2025122107000104.tif225170TIFF2025122107000105.tif226170TIFF2025122107000106.tif226170TIFF2025122107000107.tif225170TIFF2025122107000108.tif225170TIFF2025122107000109.tif225170TIFF2025122107000110.tif225170TIFF2025122107000111.tif225170TIFF2025122107000112.tif225170TIFF2025122107000113.tif226170TIFF2025122107000114.tif226170TIFF2025122107000115.tif226170TIFF2025122107000116.tif225170TIFF2025122107000117.tif226170TIFF2025122107000118.tif226170TIFF2025122107000119.tif226170TIFF2025122107000120.tif226170TIFF2025122107000121.tif228170TIFF2025122107000122.tif225170TIFF2025122107000123.tif225170TIFF2025122107000124.tif225170TIFF2025122107000125.tif225170TIFF2025122107000126.tif225170TIFF2025122107000127.tif225170TIFF2025122107000128.tif225170TIFF2025122107000129.tif225170TIFF2025122107000130.tif226170TIFF2025122107000131.tif225170TIFF2025122107000132.tif226170TIFF2025122107000133.tif225170TIFF2025122107000134.tif226170TIFF2025122107000135.tif225170TIFF2025122107000136.tif225170TIFF2025122107000137.tif228170TIFF2025122107000138.tif228170TIFF2025122107000139.tif72170.

[0182] The substituents represented by the symbols used in Table 1 are shown below. When the symbol in which Y is O in the symbol attached to the structural formula of the substituent shown below is listed in Table 1, it represents a substituent in which -Y- in the structural formula is -O- (for example, HCO-1), when the symbol in which Y is S is listed in Table 1, it represents a substituent in which -Y- in the structural formula is -S- (for example, HCS-1), and when the symbol in which Y is N is listed in Table 1, it represents a substituent in which -Y- in the structural formula is >N-Ph (Ph is phenyl) (for example, HCN-1). Furthermore, when the symbol Z in the structural formula of the substituent shown below is O and is listed in Table 1, it represents a substituent in which -Z- in the structural formula is -O- (e.g., DHCO-1), when the symbol Z is S and is listed in Table 1, it represents a substituent in which -Z- in the structural formula is -S- (e.g., DHCS-1), and when the symbol Z is N and is listed in Table 1, it represents a substituent in which -Z- in the structural formula is >N-C6D5 (e.g., DHCN-1). Furthermore, in the structural formulas below, D represents deuterium, Me represents methyl, tBu represents t-butyl, and * represents a bond position.

[0183] [ka]

[0184] [ka]

[0185] [ka]

[0186] [ka]

[0187] [ka]

[0188] [ka]

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

[0228] [ka]

[0229] [ka]

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[0255] [ka]

[0256] [ka]

[0257] 1-1-2. Method for producing anthracene compounds The anthracene compound represented by formula (1) can be produced by a method similar to the production methods described in International Publication No. 2006 / 003842, Korean Patent Publication No. 2017-116885, International Publication No. 2009 / 142230, etc.

[0258] 1-2-1. Polycyclic aromatic compounds represented by formula (2) and their multimers The organic EL device 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 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] [ka]

[0260] In each structural formula, "A" to "C" and "a" to "c" are symbols indicating a ring, a benzene ring, or a ring structure represented by a five-membered ring, and the other symbols are defined as above.

[0261] 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 atom in these rings may be substituted with a substituent. The 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, a substituted or unsubstituted aryloxy, or a substituted silyl. When these groups have a substituent, the substituent may be an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl.

[0262] In formula (2), rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent.

[0263] At least one of ring A, ring B, and ring C is preferably an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, more preferably all of ring A, ring B, and ring C are an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and 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] In this case, the substituent is preferably 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 (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. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl.

[0265] In particular, the substituent is preferably a substituted or unsubstituted alkyl (especially neopentyl) or a cycloalkyl such as adamantyl. Also preferred is a tertiary alkyl (tR). This is because such bulky substituents prevent deactivation due to aggregation of molecules and improve the luminescence quantum yield (PLQY). Also preferred as the substituent is a substituted or unsubstituted diarylamino.

[0266] The tertiary alkyl is represented by the following formula (tR): [ka]

[0267] In the formula (tR), R a , Rb , and R c are each independently alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be substituted with —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 having 1 to 24 carbon atoms" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

[0269] R in equation (tR) of equation (2) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0270] R a , R b , and R cSpecific 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 1-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, and n-eicosyl.

[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- Examples include 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, etc. Of these, t-butyl and t-amyl are preferred.

[0272] Other preferred examples of the substituents in rings A, B, and 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 "diarylamino" include the groups described below as "first substituents." Examples of the substitution of a group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include those in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with a group of formula (tR).

[0273] The aryl or heteroaryl rings in the A, B and C rings are each defined as "B", "X", 1 " and "X 2 It is preferable that the formula (2) has a 5- or 6-membered ring that shares a bond with the central fused two-ring structure.

[0274] Here, the "fused two-ring structure" refers to the two rings "B" and "X" shown in the center of formula (2). 1 " and "X 2 " means a structure in which two saturated hydrocarbon rings are fused together, each containing a ring A and a hexacyclic ring. Furthermore, "a six-membered ring sharing a bond with the fused bicyclic structure" refers to an a-ring (a benzene ring (six-membered ring)) fused to the fused bicyclic structure, as shown in, for example, formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). Furthermore, "an aryl ring or heteroaryl ring (which is ring A) has this six-membered ring" means that ring A is formed solely from this six-membered ring, or that ring A is formed by further condensing another ring to this six-membered ring so as to include this six-membered ring. In other words, "an aryl ring or heteroaryl ring (which is ring A) having a six-membered ring" means that the six-membered ring constituting all or part of ring A is fused to the fused bicyclic structure. The same explanation applies to "five-membered ring." Furthermore, the same explanation applies to "ring B (ring b)" and "ring C (ring c)."

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

[0276] X in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) Xare each independently >O, >S, >NR, or >C(-R)2. Here, R in the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, preferably an optionally substituted aryl, and more preferably an unsubstituted aryl. Furthermore, R in the >C(-R)2 is each independently hydrogen, an aryl optionally substituted with alkyl or cycloalkyl, a heteroaryl optionally substituted with alkyl or cycloalkyl, an alkyl, or a cycloalkyl, preferably an alkyl, and more preferably methyl. It is preferable that the two R in >C(-R)2 are the same. It is also preferable that the two R in >C(-R)2 together form a ring. X X are each independently preferably >O, >S, or >NR, more preferably >O or >S, and 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, diarylboryl (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 atom in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

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

[0279] R in each of formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) 1 ~R 3 In the formula, 0 to 1 of the substituents is other than hydrogen (particularly the preferred substituents described above), and the rest are hydrogen; 4 ~R 7 In the formula, 0 to 1 of the substituents is other than hydrogen (particularly the preferred substituents described above), and the rest are hydrogen; 8 ~R 11 Among them, it is preferred that 0 to 1 are other than hydrogen (particularly the above-mentioned preferred substituents) and the rest are hydrogen; R 1 ~R 3 wherein one is other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; R 4 ~R 7 wherein one is other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; R 8 ~R 11 It is more preferred that one of them is other than hydrogen (particularly the above-mentioned preferred substituents) 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 11Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (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 atom in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0281] For example, in the compound represented by formula (2-a), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring a, ring b, and ring c, as shown in the following formulas (2-a-1) and (2-a-2). Ring A', ring B', and ring C' in each formula correspond to ring A, ring B, and ring C in formula (2), respectively. In addition, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 , a, b, c, X 1 and X 2 The definition of is the same as that in formula (2-a).

[0282] [ka]

[0283] The A' ring, B' ring, and C' ring in the formula (2-a-1) and the formula (2-a-2) are each independently a substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8, R 9 , R 10 , and R 11 Adjacent groups among these are bonded to form an aryl or heteroaryl ring together with the a, b, and c rings, respectively (this can also be considered a fused ring formed by fusing other ring structures to the a, b, or c ring). Although not shown in the formula, there are also compounds in which all of the a, b, and c rings are changed to A', B', and C' rings. Also, as can be seen from formula (2-a-1) and formula (2-a-2), for example, R of the b ring 8 and R in c-ring 7 , b-ring R 11 and a-ring R 1 , R of ring c 4 and a-ring R 3 etc. are not considered to be "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" means groups that are adjacent on the same ring.

[0284] The compounds represented by formula (2-a-1) and formula (2-a-2) correspond to, for example, compounds represented by formulas (2-67) to (2-74), (2-76) to (2-83), (2-273) to (2-276), (2-290) to (2-295), and (2-350) to (2-355), which are listed below as specific compounds. That is, for example, it is a compound having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c) in formula (2-a), with a benzene ring, indole ring, pyrrole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, cyclopentadiene ring, or indene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') formed is a naphthalene ring, carbazole ring, indole ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, indene ring, or fluorene ring, respectively.

[0285] Similarly, in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), a fused ring may be formed by condensing another ring structure to ring a, ring b, or ring c. For example, the benzene ring that is ring a or ring b may be condensed with another ring structure to form a fused ring, similar to the benzene ring in formula (1-a).

[0286] In the formulae (2-b), (2-c), (2-d), (2-e), and (2-f), in the 5-membered ring which is the b-ring or the c-ring, R 4 ~R 11 It is particularly preferred that adjacent groups among these are bonded to form a ring to form a fused ring. For example, in the ring c of formula (2-b) and formula (2-c), and the ring b and ring c of formula (2-d), formula (2-e), and formula (2-f), R 3 ~R 11 Adjacent groups among these can be bonded to form a ring, forming a fused ring, ring B' or ring C'. Examples of fused rings in which the ring formed 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 formulas (2-572) to (1-588) described below.

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

[0288] As an example, in the five-membered ring that is the ring c of formula (2-b), R 4 and R 5 Examples of fused rings formed by bonding together to form a benzene ring are shown below. [ka]

[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 R has the same meaning as each of the groups in formula (2-b), and the preferred ranges are also the same. 4b , R 5b , R 6b , R 7b is a hydrogen atom or a substituent selected from the group consisting of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (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 atom in these substituents may be replaced 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 rest are hydrogen, and it is more preferable that one is a substituent other than hydrogen and the rest are hydrogen. For a preferable range of the substituent other than hydrogen, reference can be made to the description of the substituent below as the first substituent (which may have a second substituent). Particularly preferable substituents other than hydrogen are alkyl (particularly the above-mentioned tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0290] X in equation (2) 1 and X 2 are each independently >O, >NR, >C(-R)2, >S, or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >NR and / or R of the >C(-R)2 may be bonded to the B ring and / or the C ring via a linking group or a single bond, and the linking group is preferably -O-, -S-, or -C(-R)2-. Note that R of the "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 But it's the same.

[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 preferably independently >O or >NR, more preferably >NR where R is an optionally substituted phenyl, even more preferably >NR where at least one R is a phenyl substituted with one or two t-butyl, t-amyl, methyl or phenyl, and particularly preferably >NR where at least one R is a phenyl substituted with one t-butyl or t-amyl. 1 and X 2 may be the same group or different groups.

[0292] Here, the provision in formula (2) that "R of >NR and / or R of >C(-R)2 are bonded to ring A, ring B, and / or ring C via a linking group or a single bond" corresponds to the provision in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) that "R of >NR and / or R of >C(-R)2 are bonded to ring a, ring b, and / or ring c via -O-, -S-, -C(-R)2- or a single bond."

[0293] This rule is expressed by the following formula (2-a-3-1), X 1 or X 2 can be expressed as a compound having a ring structure in which X is incorporated into the fused ring B' and the fused ring C'. That is, for example, the compound having X in the ring b (or ring c) of the benzene ring in formula (2-a) 1 (or X 2 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring B'. The condensed ring B' (or condensed ring C') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0294] In addition, the above provisions are based on the following formulas (2-a-3-2) and (2-a-3-3): 1 and / or X 2 It can also be expressed as a compound having a ring structure in which X is incorporated into the fused ring A'. That is, for example, with respect to the benzene ring which is the a ring in formula (2-a), 1 (and / or X 2 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0295] [ka]

[0296] The "aryl ring" which is the ring A, ring B, and ring C in formula (2) is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. The "aryl ring" includes the benzene ring in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), and "R 1 ~R 11 The aryl ring corresponds to "an aryl ring formed together with ring a, ring b, or ring c by bonding adjacent groups among the above."

[0297] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and a tetralin ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) and a fused tricyclic anthracene ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, fused tetracyclic triphenylene ring, a pyrene ring, and a naphthacene ring, fused pentacyclic perylene ring and a pentacene ring, and the like.

[0298] Examples of the "heteroaryl ring" which is the ring A, ring B, and ring C in 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, even more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. In addition, examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. The "heteroaryl ring" includes the 5-membered rings in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), and "R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R10 , and R 11 The heteroaryl ring formed by bonding adjacent groups among the above together with ring a, ring b, or ring c corresponds to "a heteroaryl ring."

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

[0300] In the above, the "aryl ring" and "heteroaryl ring" which are rings A, B and 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). Of these, as mentioned above, rings A, B and C may share a bond with B, X 1 , and X 2 It is preferable that the formula (2-a) has a 5-membered ring or a 6-membered ring that shares a bond with the central fused two-ring structure. 1 ~R 3 , R 4 ~R 7 , and R 8 ~R 11When adjacent groups among these are bonded to each other to form an aryl ring or heteroaryl ring together with ring a, ring b, or ring c (the 6-membered benzene ring shares a bond with the central fused two-ring structure of formula (2)), and R in formula (2-b), (2-c), formula (2-d), formula (2-e), or formula (2-f) 4 ~R 11 It is preferable that adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with rings b and c (a five-membered ring that shares a bond with the central fused two-ring structure of formula (2)). Examples of the five-membered ring in this case include a pyrrole ring, a furan ring, and a thiophene ring.

[0301] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl," a substituted or unsubstituted "heteroaryl," a substituted or unsubstituted "diarylamino," a substituted or unsubstituted "diheteroarylamino," a substituted or unsubstituted "arylheteroarylamino," a substituted or unsubstituted "diarylboryl (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," a substituted or unsubstituted "aryloxy," or a substituted silyl. Examples of the "aryl" or "heteroaryl" as the first substituent, the aryl of "diarylamino," the heteroaryl of "diheteroarylamino," the aryl and heteroaryl of "arylheteroarylamino," the aryl of "diarylboryl," and the aryl of "aryloxy" include the monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0302] Furthermore, the "alkyl" as the first substituent 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 even more preferred, and alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is particularly preferred.

[0303] Specific alkyl groups 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, and 1-methylheptyl. Examples of the alkyl ether include 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, and n-eicosyl.

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

[0305] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as 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, and decahydroazulenyl.

[0306] Furthermore, examples of the "alkoxy" as the first substituent include straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 4 carbon atoms (branched-chain 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, and octyloxy.

[0308] Furthermore, 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, such as trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0309] An example of a "trialkylsilyl" is a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl group, and the alkyl group can be any of the groups described above as the "alkyl" in the first substituent. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0310] Specific examples of trialkylsilyl 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-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butylsilyl. Examples thereof include butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0311] Examples of "tricycloalkylsilyl" include a group in which three hydrogen atoms in silyl are each independently substituted with a cycloalkyl, and examples of this cycloalkyl include the groups described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0312] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0313] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the above-mentioned specific alkyls and cycloalkyls.

[0314] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0315] Furthermore, the "aryl" in the "diarylboryl" as the first substituent can be referenced from the above description of the aryl. Furthermore, the two aryls may be bonded via a single bond or a linking group (for example, >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl (all of which are first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl (all of which are second substituents). Specific examples of these groups can be referenced from the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

[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, and is preferably a group represented by the following structural formula, more preferably methyl, t-butyl, t-pentyl (t-amyl), t-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)phenyl), phenyl, ... Preferred are 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 preferred for selective synthesis, and 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 preferred.

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

[0318] [ka]

[0319] [ka]

[0320]

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[0321]

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[0322]

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[0323]

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[0324]

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[0325]

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[0326]

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[0327]

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[0328]

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[0329]

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[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 Among these, it is preferred that 1 to 4 are groups represented by any of the structural formulas above, and the rest are hydrogen; 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 R are groups represented by any of the structural formulas above, and the rest are hydrogen. 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 these are methyl, t-butyl or t-amyl, and the remainder are hydrogen.

[0331] As described above for the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (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", or substituted or unsubstituted "aryloxy" may have at least one hydrogen atom substituted with a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, and specific examples thereof can be found in the descriptions of the monovalent groups of the "aryl ring" or "heteroaryl ring" described above, and the "alkyl", "cycloalkyl", or substituted silyl as the first substituent. Furthermore, the aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl or heteroaryl is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are the groups described above), or a cycloalkyl such as cyclohexyl (specific examples are the groups described above). For example, when the second substituent is carbazolyl, a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also included in the 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 11The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, or aryl of aryloxy in the formula (1) include the monovalent groups of "aryl ring" or "heteroaryl ring" explained in formula (2). 1 ~R 11 For the alkyl, cycloalkyl, or alkoxy in R, the explanation of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent in the explanation of formula (2) above can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl as substituents on these groups. 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 these are bonded to form an aryl ring or heteroaryl ring together with ring a, ring b, or ring c, the same applies to the heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, or aryloxy that are substituents on these rings, and the aryl, heteroaryl, alkyl, or cycloalkyl that are further substituents.

[0333] X in equation (2) 1 and X 2In the formula (2-a), R in >NR is aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen atom in the aryl or heteroaryl may be substituted with, for example, alkyl, cycloalkyl, or substituted silyl. Examples of the aryl, heteroaryl, alkyl, and cycloalkyl include the groups described above. In particular, 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) are preferred. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 The same is true for X in equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 R in >NR 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 is preferably an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.

[0334] X in equation (2) 1 and X 2In the formula (2-a), R in >C(-R)2 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 the aryl, alkyl, and cycloalkyl include the groups described above. In particular, 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) are preferred. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 The same is true for X in equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 R in >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 is preferably hydrogen, 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.

[0335] In formula (2), R in the linking group "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl, and examples of the alkyl and cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation also applies to the linking group "-C(-R)2-" in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (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 polymer may be in any form as long as it has a plurality of the above unit structures in one compound. For example, in addition to a form in which a plurality of the above unit structures are bonded together via a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group, the polymer may be in a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be shared by the plurality of unit structures, or in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be fused.

[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). The symbols in these formulas have the same meanings as those in formula (2-a), and the preferred ranges are also the same. The multimer compound represented by the following formula (2-4), when explained in terms of formula (2-a), is a multimer compound having multiple unit structures represented by formula (2-a) in one compound, with the benzene ring (a) being shared. Furthermore, the multimer compound represented by the following formula (2-4-1), when explained in terms of formula (2-a), is a multimer compound having two unit structures represented by formula (2-a) in one compound, with the benzene ring (a) being shared. Furthermore, the multimeric compound represented by the following formula (2-4-2) is a multimeric compound having three unit structures represented by formula (2-a) in one compound, with the benzene ring (a) being shared among them. Furthermore, the multimeric compounds represented by the following formulas (2-5-1) to (2-5-4) are multimeric compounds having a plurality of unit structures represented by formula (2) in one compound, with the benzene ring (b) being shared among them. Furthermore, the multimeric compound represented by the following formula (2-6) is a multimeric compound having a plurality of unit structures represented by formula (2-a) in one compound, with the benzene ring (b) being shared among them. Furthermore, the multimeric compound represented by the following formula (2-a) is a multimeric compound having a plurality of unit structures represented by formula (2-a) in one compound, with the benzene ring (b) being shared among them.

[0338] [ka]

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

[0340] In addition, all or part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound and its multimer represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) may be deuterium, cyano, or halogen. For example, in formula (2), the A ring, the B ring, and the C ring (A to C rings are aryl rings or heteroaryl rings), the substituents on the A to C rings, and X 3 and X 4 When >NR or >C(-R)2, hydrogen atoms in R (= alkyl, cycloalkyl, aryl) can be substituted with deuterium, cyano, or halogen atoms, and among these, embodiments in which all or part of the hydrogen atoms in the aryl or heteroaryl are substituted with deuterium, cyano, or halogen atoms are exemplified. Halogen atoms are fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and 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 structure 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 multimers thereof may be condensed with at least one cycloalkane.

[0342] For example, aryl and heteroaryl rings in the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents in ring A to ring C, aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a, ring b, and ring c, and X 1 , X 2 At least one of >NR, and aryl (as above) and heteroaryl (as above) as R in >C(—R)2 may be fused with at least one cycloalkane.

[0343] Preferably, the aryl and heteroaryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; aryl (aryl moiety in aryl, diarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents in ring A to ring C; aryl (similar to above) and heteroaryl (similar to above) as the first substituents on ring a to ring c; and X 1 , X 2 At least one of the aryl (similar to above) and heteroaryl (similar to above) as R in >NR and >C(—R) 2 may be fused with at least one cycloalkane.

[0344] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents in ring A to ring C; the aryl (similar to above) and heteroaryl (similar to above) as the first substituents on ring a, ring b, and ring c; and X 1 , X 2At least one of >NR, which is: and aryl (as above) as R in >C(—R) 2 may be fused with at least one cycloalkane.

[0345] More preferred are aryl rings which are 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 or aryl moiety in diarylamino), aryl as the first substituent on ring a, ring b, and ring c (similar to above), and X 1 , X 2 At least one of >NR, which is: and aryl (as above) as R in >C(—R) 2 may be fused with at least one cycloalkane.

[0346] Examples of "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, as well as alkyl (particularly methyl)-substituted, halogen (particularly fluorine)-substituted, and deuterium-substituted derivatives of these compounds having 1 to 5 carbon atoms.

[0348] Among these, a structure in which at least one hydrogen atom is substituted on the α-carbon atom of the cycloalkane (in a cycloalkyl fused to an aromatic ring or heteroaromatic ring, the carbon atom adjacent to the fused carbon atom) is preferred, a structure in which two hydrogen atoms are substituted on the α-carbon atom is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two α-carbon atoms is even more preferred. Examples of such a substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.

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

[0350] [ka]

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

[0352] [ka]

[0353] The number of cycloalkanes fused 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 in which one or more cycloalkanes are fused to one benzene ring (phenyl) are shown below. Fused cycloalkanes such as those in formula (Cy-1-4) and formula (Cy-2-4) may be fused together. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0354] [ka]

[0355] At least one -CH2- in a cycloalkane may be replaced with -O-. For example, an example in which one or more -CH2- in a cycloalkane fused to a benzene ring (phenyl) are replaced with -O- is shown below. The same applies even when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0356] [ka]

[0357] At least one hydrogen atom in the cycloalkane may be substituted. Examples of the substituent 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, and halogen. For details, see the description of the first substituent above. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when cycloalkyl is substituted, it may be substituted to form a spiro structure, examples of which are shown below.

[0358] [ka]

[0359] Other forms of cycloalkane condensation include 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 multimers thereof, such as >NR, where R is an aryl fused with a cycloalkane, diarylamino fused with a cycloalkane (fused to this aryl moiety), carbazolyl fused with a cycloalkane (fused to this benzene ring moiety), or benzocarbazolyl fused with a cycloalkane (fused to this benzene ring moiety). Examples of "diarylamino" include the groups described above as the "first substituent."

[0360] Further, more specific examples include R in polycyclic aromatic compounds and multimers thereof represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). 2 is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0361] More specific examples of polycyclic aromatic compounds represented by formula (2) include compounds represented by the following formula: In the following formula, "Me" represents methyl, "tBu" represents t-butyl, "iPr" represents isopropyl, "Ph" represents phenyl, "tAm" represents t-amyl (tertiary pentyl), and "D" represents deuterium.

[0362] [ka]

[0363] [ka]

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367] [ka]

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371]

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[0375]

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[0377]

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[0378]

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[0379]

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[0380]

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[0381]

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[0382]

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[0383]

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[0384]

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[0386]

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[0387]

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[0389]

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[0390]

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[0391]

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[0399]

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[0403] [ka]

[0404] [ka]

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

[0406] 1-3.Emitting layer The light-emitting layer may be a single layer or multiple layers, each formed from materials for the light-emitting layer (host material, dopant material). The host material may be a single 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 a single compound represented by formula (1) or a combination of two or more compounds represented by formula (1). The dopant material may be a single 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 a single compound represented by formula (2) or a combination of two or more compounds represented by formula (2).

[0407] The dopant material may be contained entirely or partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, or the dopant material may be mixed with the host material in advance and then evaporated simultaneously.

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

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

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

[0411] Dopant materials that can be used in combination with the compound represented by formula (2) include fused ring derivatives of anthracene and pyrene, which have long been known as light 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 organic electroluminescent devices The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via 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 or mixing one or more electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0413] The electron injection / transport layer is a layer responsible for injecting electrons from the cathode and transporting them. It is desirable for the layer to have high electron injection efficiency and efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and be less likely to generate trapping impurities during manufacture and use. However, considering the balance between hole and electron transport, if a material primarily serves to efficiently block holes from the anode from flowing to the cathode without recombining, it can have the same effect of improving luminous efficiency as a material with high electron transport ability, even if it does not have a particularly high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also function as a layer that can efficiently block the movement of holes.

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

[0415] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from the group consisting of aromatic or heteroaromatic ring compounds composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused ring derivatives; and metal complexes containing electron-accepting nitrogen. Specific examples include fused ring aromatic derivatives such as naphthalene and anthracene; styryl aromatic derivatives such as 4,4'-bis(diphenylethenyl)biphenyl; perinone derivatives; coumarin derivatives; naphthalimide derivatives; quinone derivatives such as anthraquinone and diphenoquinone; phosphine oxide derivatives; arylnitrile derivatives; and indole derivatives. Metal complexes containing electron-accepting nitrogen include, for example, 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 other materials.

[0416] Specific examples of other electron transfer compounds include borane derivatives, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and 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, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0417] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0418] The above-mentioned materials may be used alone or in combination with other 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, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0420] <Borane derivatives> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka]

[0421] In formula (ETM-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; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or fewer carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

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

[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; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an 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 represents an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0424] [ka]

[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; R 13 ~R 16are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an arylene having 20 or less carbon atoms which may be substituted, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0426] X 1 Specific examples of include divalent groups represented by any of the following formulae (X-1) to (X-9). [ka] (In each formula, R a are each independently alkyl, cycloalkyl or optionally substituted phenyl, and * represents the bonding position.

[0427] Specific examples of the borane derivative include the following compounds: [ka]

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

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

[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 of 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 be bonded to form a ring.

[0433] In each formula, the "pyridine-based substituent" is any of the following formulae (Py-1) to (Py-15) (in the formula, * represents a bonding position), and each pyridine-based substituent may be independently 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, and t-butyl, with methyl being preferred. In addition, the pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene group or naphthylene group.

[0434] [ka]

[0435] The pyridine-based substituent is any of the formulae (Py-1) to (Py-15), and among these, any of the following formulae (Py-21) to (Py-44) (in the formulae, * represents the bonding position) is preferable. [ka]

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

[0437] R 11 ~R 18 The "alkyl" in the above 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. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched 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, Examples include 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, and n-eicosyl.

[0439] The above description of alkyl can be cited for the alkyl having 1 to 4 carbon atoms that substitutes the pyridine-based substituent.

[0440] R 11 ~R 18 Examples of the "cycloalkyl" in the above include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An 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, and dimethylcyclohexyl.

[0441] R 11 ~R 18 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is 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 fused bicyclic aryl; acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl, which are fused tricyclic aryl; triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, which are fused tetracyclic aryl; and perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl, which are fused pentacyclic aryl.

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

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

[0445] Specific examples of the pyridine derivative include the following compounds: [ka]

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

[0447] <Fluoranthene derivatives> 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 when it is 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 a polycyclic aromatic compound represented by, for example, 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 these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen atom in these rings may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

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

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

[0455] Specific examples of the BO derivative include the following compounds: [ka]

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

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

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

[0459] Ar 2are each 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 "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl; bicyclic aryls such as (2-, 3-, 4-)biphenylyl; fused bicyclic aryls such as (1-, 2-)naphthyl; tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-ter phenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryls such as anthracene-(1-, 2-, 9-)yl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

[0460] R 1 ~R 4 are each 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 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. It is more preferably an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl is preferred, and methyl, ethyl, or t-butyl is more preferred.

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

[0463] R 1 ~R 4 In the above, the aryl having 6 to 20 carbon atoms is 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 "aryl having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryl having 6 to 20 carbon atoms" in the above can be cited. Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, and naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, and m-terphenyl-5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl, and 2-naphthyl, and most preferably phenyl.

[0464] Specific examples of these anthracene derivatives include the following compounds: [ka]

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

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

[0467] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and Ar in formula (ETM-5) 2 The same explanation as for "aryl having 6 to 20 carbon atoms" in the above 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, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0468] Ar 2 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 two Ar 2 may be bonded to form a ring.

[0469] Ar 2The "alkyl" in the above 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. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched 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, and 1-methylhexyl.

[0470] Ar 2 In the above, "cycloalkyl" 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, and dimethylcyclohexyl.

[0471] Ar 2 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is 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, and pentacenyl.

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

[0474] Specific examples of the benzofluorene derivative include the following compounds: [ka]

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

[0476] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): Details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[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 of 0 to 4, and q is an integer of 1 to 3. When substituted, the substituent may be an aryl, heteroaryl, alkyl, or cycloalkyl.

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

[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, aryl thioether group, aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

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

[0481] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. When substituted, the substituent is not particularly limited, and examples thereof include alkyl, aryl, and heterocyclic groups, which also apply to the following description. The number of carbon atoms in the alkyl is not particularly limited, but is usually in the range of 1 to 20 from the viewpoints of availability and cost.

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

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

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

[0485] Furthermore, 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] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be substituted or unsubstituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually in the range of 2 to 20.

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

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

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

[0490] The aryl ether group refers to an aromatic hydrocarbon group such as phenoxy, which is bonded via an ether bond, and the aromatic hydrocarbon group may be substituted or unsubstituted. 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] 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] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, or pyrenyl. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0493] The heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which 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] Formyl, carbonyl and amino may also include groups substituted with an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocycle or the like.

[0496] The aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocyclic rings may be either unsubstituted or substituted.

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

[0498] The fused 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 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings with each other. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0499] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

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

[0501] <Pyrimidine derivatives> 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 WO 2011 / 021689. [ka]

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

[0503] The "aryl" in "optionally substituted aryl" includes, for example, 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.

[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 fused 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), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0505] 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. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0506] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0507] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0508] Specific examples of the pyrimidine derivative include the following compounds: [ka]

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

[0510] <Arylnitrile derivatives> The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded via single bonds, etc. Details are described in the specification of U.S. Application Publication No. 2014 / 0197386. [ka]

[0511] Ar niFrom the viewpoint of fast electron transporting property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, when used in a layer adjacent to the light-emitting layer, it is preferable that the aryl group has a high T1, and is an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 14 carbon atoms, and more preferably an aryl having 6 to 10 carbon atoms. Furthermore, the number of nitrile group substitutions, n, is preferably large from the viewpoint of a high T1, and is preferably small from the viewpoint of a high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 or 2, and even more preferably 1.

[0512] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. From the viewpoint of high S1 and high T1, donor heteroaryl is preferred, and since it is used as an electron transport layer, it is preferred that there are fewer donor heteroaryls. From the viewpoint of charge transportability, aryl or heteroaryl with a large number of carbon atoms is preferred, and it is preferred that there are many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[0513] The "aryl" in "optionally substituted aryl" includes, for example, 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.

[0514] 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 fused 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), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[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. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0516] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0517] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0518] The aryl nitrile derivative may be a polymer in which a plurality of compounds represented by formula (ETM-9) are bonded together via single bonds, etc. In this case, they may be bonded together via an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

[0519] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0520] The arylnitrile derivative can be produced using known raw materials and known synthesis methods.

[0521] <Triazine derivatives> 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), the details of which are described in the specification of U.S. Patent Application Publication No. 2011 / 0156013. [ka]

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

[0523] The "aryl" in "optionally substituted aryl" includes, for example, 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 "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused 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), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0525] 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. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0526] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0527] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0528] Specific examples of the triazine derivative include the following compounds: [ka]

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

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

[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 of 1 to 4, and the "benzimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0532] [ka]

[0533] R in the 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 R in formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[0534] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine-based substituents are bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be replaced with .

[0535] Specific examples of the benzimidazole derivative include 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, and 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] [ka]

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

[0538] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982.

[0539] [ka]

[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 of 1 to 4.

[0541] R in each formula 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). 11 ~R 18 Either of these bonds becomes a bond to the aryl ring φ.

[0542] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0543] R 11 ~R 18 The alkyl, cycloalkyl and aryl in formula (ETM-2) include R 11 ~R 18 can be cited. In addition to the examples given above, φ can have the following structural formula: In the structural formula, each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates the bonding position.

[0544] [ka]

[0545] Specific examples of the phenanthroline derivative include 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-bi(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] [ka]

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

[0548] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, Ga, Be, or Zn; and n is an integer of 1 to 3.

[0549] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, 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)(phenolate)aluminum, and bis(2-methyl-8-quinolinolato). Bis(2-methyl-8-quinolinolate)(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum linolinolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- Examples include bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, and bis(10-hydroxybenzo[h]quinoline)beryllium.

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

[0552] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4. A "thiazole-based substituent" or a "benzothiazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the following thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative or benzothiazole derivative may be replaced with deuterium.

[0553] [ka]

[0554] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine-based substituents are bonded, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be replaced with .

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

[0556] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0557] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, see the explanations for formula (1) and formula (2) and also the explanation for formula (ETM-7-2). Furthermore, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, see the explanation for formula (ETM-7-2). Furthermore, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a portion is unsaturated), and details of this cycloalkyl ring can be found in the explanation of cycloalkyl in formula (1) and formula (2).

[0558] R 1 ~R 4are each independently 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 fused ring with an adjacent substituent.

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

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

[0561] Examples of silyl include unsubstituted silyl and groups in which at least one of three hydrogen atoms of silyl is independently substituted with an aryl, alkyl, or cycloalkyl, and tri-substituted silyl is preferred, including triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, etc. For details of the aryl, alkyl, and cycloalkyl in these, the explanations in formula (1) and formula (2) can be cited.

[0562] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0563] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R is 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 and R are preferably cycloalkyl groups that do not simultaneously satisfy the condition that R 1 and R 4 If is Cyril, then R 2 , R 3 , X and Y are not each independently hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is fused with X, X and Y are not alkyl and phenyl.

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

[0565] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in WO 2017 / 014226. [ka]

[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 heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -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 atom 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, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and the R 1 ~R 5 one of which is a binding site for L, L's are each 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] [ka]

[0568] In formula (L-1), X 1 ~X 6are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the 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 them are =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom in 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; m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom 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 (ETM-16-2). [ka]

[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 heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -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 atom of Ar is optionally 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, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 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 identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), L's are each 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] [ka]

[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 -R in 6 is the bonding site with φ or the 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 them are =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom in 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; m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom 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 formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen atom of φ may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms.

[0574] [ka]

[0575] [ka]

[0576] [ka]

[0577] In the formula, Z is >CR2, >N-Ar, >NL, -O-, or -S-, and each R in >CR2 is independently 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 each other 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 >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). * in the formula indicates the bonding position.

[0578] Preferably, L is a divalent ring group 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 atom 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 atom 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 identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen atoms at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0581] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka] [ka]

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

[0583] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen atom of L is optionally 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 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of Ar 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; 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 identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same.

[0584] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0585] For details of alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations for 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 substances> 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. A variety of reducing substances can be used as this reducing substance as long as they have a certain level of reducing ability. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0588] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), and Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), and Ba (2.52 eV), with those with a work function of 2.9 eV or less being particularly preferred. Of these, more preferred reducing substances are alkali metals such as K, Rb, and Cs, with Rb or Cs being even more preferred, and Cs being the most preferred. These alkali metals have particularly high reducing ability, and adding a relatively small amount of them to the material forming the electron transport layer or electron injection layer can improve the luminance and extend the life of the organic EL device. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs, Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and the lifetime can be extended.

[0589] 3. Substrate for organic electroluminescent device The substrate 101 serves as a support for the organic EL device 100 and is typically made of quartz, glass, metal, plastic, or the like. The substrate 101 may be formed into a plate, film, or sheet shape depending on the purpose, and may be, for example, a glass plate, a metal plate, a metal foil, a plastic film, or a plastic sheet. Among these, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. For glass substrates, soda-lime glass or alkali-free glass may be used, and the thickness should be sufficient to maintain mechanical strength, e.g., 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it minimizes ion elution from the glass. However, commercially available soda-lime glass coated with a barrier coating such as SiO2 can also be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof, and it is particularly preferable to provide a gas barrier film when a synthetic resin plate, film, or sheet with poor gas barrier properties is used as the substrate 101.

[0590] 4. Anode in organic electroluminescent device The anode 102 serves to inject holes into the light-emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

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

[0592] The resistance of the transparent electrode is not limited as long as it can supply sufficient current to light the light-emitting element, but low resistance is desirable from the perspective of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / □ or less can function as an element electrode, but since substrates with a resistance of about 10 Ω / □ are now available, it is particularly desirable to use a low resistance product with a resistance of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be selected arbitrarily depending on the resistance value, but it is usually between 50 and 300 nm.

[0593] 5. Hole injection layer and hole transport layer in organic electroluminescent devices The hole injection layer 103 serves to efficiently inject holes migrating 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 via 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. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0594] A hole injection / transport material must be able to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. To achieve this, it is desirable for the material to have a low ionization potential, high hole mobility, excellent stability, and be less likely to generate impurities that act as traps during production and use.

[0595] Materials for forming the hole injection layer 103 and the hole transport layer 104 can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known materials used in hole injection layers and hole transport layers of organic EL devices. 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-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]- Examples of suitable polymers include triphenylamine derivatives such as 4-amine, starburst amine derivatives, stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymers, polycarbonates and styrene derivatives, polyvinylcarbazole, and polysilanes having the above-mentioned monomers in their side chains are preferred, but the polymers are not particularly limited as long as they can form a thin film necessary for fabricating a light-emitting device, inject holes from the anode, and transport holes.

[0596] It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix materials consist of compounds with good electron-donating or electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes via an electron transfer process in the electron-donating base material (hole-transporting material). The conductivity of the base material varies considerably depending on the number and mobility of holes. Known matrix materials with hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), as well as certain metal phthalocyanines (e.g., zinc phthalocyanine (ZnPc)) (see JP 2005-167175 A).

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

[0598] The material for the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same materials as those for the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum alloys), are preferred. To increase electron injection efficiency and improve device characteristics, 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 air. To address this issue, a method has been proposed in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to create a highly stable electrode. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, the present invention is not limited to these.

[0599] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is not particularly limited as long as electrical conduction can be achieved, and may include resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

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

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

[0602] Next, as an example of a method for fabricating an organic EL device, we will explain a method for fabricating an organic EL device consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer composed of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. A thin film of an anode material is formed on a suitable substrate by vapor deposition or other methods to form an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A thin film of a host material and a dopant material is co-deposited on the anode to form an emitting layer. An electron transport layer and an electron injection layer are then formed on the emitting layer, and a thin film of a cathode material is further formed by vapor deposition or other methods to form a cathode, thereby obtaining the desired organic EL device. It should be noted that the above-described organic EL device can also be fabricated in the reverse order: cathode, electron injection layer, electron transport layer, emitting layer, hole transport layer, hole injection layer, and anode.

[0603] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. 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, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the applied AC current can be any waveform.

[0604] <<Application examples of organic electroluminescent devices>> The present invention can also be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example, by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0605] Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, and JP-A-2004-281086). Examples of display methods include matrix and / or segment methods. Note that matrix display and segment display may coexist in the same panel.

[0606] A matrix is a display device in which pixels are arranged two-dimensionally, such as in a grid or mosaic pattern, to display characters and images. The shape and size of the pixels are determined by the application. For example, images and text displayed on computers, monitors, and televisions typically use square pixels with sides of 300 μm or less. Large displays such as display panels use pixels with sides on the order of millimeters. For monochrome displays, pixels of the same color are simply arranged, while for color displays, red, green, and blue pixels are arranged side by side. These types are typically known as delta and stripe types. The matrix can be driven by either line-sequential or active matrix methods. While line-sequential driving has the advantage of being simpler, active matrix methods can sometimes be superior in terms of operating characteristics, so the choice must be made based on the application.

[0607] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include the time and temperature displays on digital clocks and thermometers, the operating status displays on audio equipment and induction cookers, and panel displays on automobiles.

[0608] Examples of lighting devices include lighting devices for indoor lighting and backlights for liquid crystal display devices (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are primarily used to improve the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for backlights of liquid crystal display devices, particularly those used for personal computers, where thinning is an issue, conventional backlights are difficult to achieve because they are made of fluorescent lamps and light guide plates. Therefore, backlights using the light-emitting elements according to this embodiment are characterized by their thinness and light weight. [Example]

[0609] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these. First, synthesis examples of compounds used in the examples will be described below.

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

[0611] Compound (1-1) was synthesized according to the method described in WO 2006 / 003842.

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

[0613] Compound (1-12) was synthesized according to the method described in WO 2006 / 003842.

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

[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) [ka]

[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) [ka]

[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) [ka]

[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) [ka]

[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) [ka]

[0625] Compound (1-319) was synthesized according to the method described in WO 2006 / 003842.

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

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

[0628] [ka]

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

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

[0631] [ka]

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

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

[0634] [ka]

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

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

[0637] [ka]

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

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

[0640] [ka]

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

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

[0643] [ka]

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

[0645] Compound (1-641) was synthesized according to the method described in WO 2009 / 142230.

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

[0647] Compound (1-646) was synthesized according to the method described in WO 2009 / 142230.

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

[0649] Compound (1-649) was synthesized according to the method described in WO 2009 / 142230.

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

[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) [ka]

[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) [ka]

[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) [ka]

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

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

[0659] Compound (1-682) was synthesized by appropriately changing the starting compounds of the method described in WO 2009 / 142230. EI-MS: m / z=784.

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

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

[0662] [ka]

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

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

[0665] [ka]

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

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

[0668] [ka]

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

[0670] Compound (1-125) was synthesized according to the method described in WO 2006 / 003842.

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

[0672] Compound (1-155) was synthesized according to the method described in WO 2006 / 003842.

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

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

[0675] [ka]

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

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

[0678] [ka]

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

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

[0681] [ka]

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

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

[0684] [ka]

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

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

[0687] [ka]

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

[0689] Compound (1-124) 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.

[0690] [ka]

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

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

[0693] [ka]

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

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

[0696] [ka]

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

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

[0699] [ka]

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

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

[0702] [ka]

[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] [ka]

[0711] Synthesis Example (1-42): Synthesis of Compound (1-136) Compound (1-136) 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.

[0712] [ka]

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

[0714] [ka]

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

[0716] [ka]

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

[0718] [ka]

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

[0720] [ka]

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

[0722] [ka]

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

[0724] [ka]

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

[0726] [ka]

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

[0728] [ka]

[0729] Synthesis Example (1-51): Synthesis of Compound (1-4327) Compound (1-4327) 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.

[0730] [ka]

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

[0732] [ka]

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

[0734] [ka]

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

[0736] [ka]

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

[0738] [ka]

[0739] Synthesis Example (1-56): Synthesis of Compound (1-4205) Under a nitrogen atmosphere, intermediate (I-2) (1.0 g) was dissolved in toluene (100 ml), and 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. The mixture was heated and stirred under reflux for 5 hours. After the reaction, water was added to the reaction mixture to quench the reaction. Toluene was then added for liquid separation and extraction. The organic layer was then concentrated to obtain the crude product. The resulting crude product was purified using a silica gel short column (eluent: chlorobenzene) to obtain compound (1-4205) (0.85 g). EI-MS: m / z = 608.

[0740] [ka]

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

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

[0743] [ka]

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

[0745] [ka]

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

[0747] [ka]

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

[0749] [ka]

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

[0751] [ka]

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

[0753] [ka]

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

[0755] [ka]

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

[0757] [ka]

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

[0759] [ka]

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

[0761] [ka]

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

[0763] [ka]

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

[0765] [ka]

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

[0767] [ka]

[0768] Synthesis Example (1-71): Synthesis of Compound (1-4093) Compound (1-4093) 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.

[0769] [ka]

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

[0771] [ka]

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

[0773] [ka]

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

[0775] [ka]

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

[0777] [ka]

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

[0779] [ka]

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

[0781] [ka]

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

[0783] [ka]

[0784] Synthesis Example (1-79): Synthesis of Compound (1-4106) Compound (1-4106) 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.

[0785] [ka]

[0786] Synthesis Example (1-80): Synthesis of Compound (1-3830) Compound (1-3830) 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.

[0787] [ka]

[0788] Synthesis Example (1-81): Synthesis of Compound (1-3839) Compound (1-3839) 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.

[0789] [ka]

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

[0791] [ka]

[0792] Synthesis Example (1-83): Synthesis of Compound (1-4390) Compound (1-4390) 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.

[0793] [ka]

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

[0795] [ka]

[0796] Synthesis Example (1-85): Synthesis of Compound (1-4091) Compound (1-4091) 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.

[0797] [ka]

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

[0799] [ka]

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

[0801] [ka]

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

[0803] [ka]

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

[0805] [ka]

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

[0807] [ka]

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

[0809] [ka]

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

[0811] [ka]

[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] [ka]

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

[0815] [ka]

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

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

[0818] [ka]

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

[0820] [ka]

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

[0822] [ka]

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

[0824] [ka]

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

[0826] [ka]

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

[0828] [ka]

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

[0830] [ka]

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

[0832] [ka]

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

[0834] [ka]

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

[0836] [ka]

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

[0838] [ka]

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

[0840] [ka]

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

[0842] [ka]

[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] [ka]

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

[0846] [ka]

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

[0848] [ka]

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

[0850] [ka]

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

[0852] [ka]

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

[0854] [ka]

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

[0856] [ka]

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

[0858] [ka]

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

[0860] [ka]

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

[0862] [ka]

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

[0864] [ka]

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

[0866] [ka]

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

[0868] [ka]

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

[0870] [ka]

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

[0872] [ka]

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

[0874] [ka]

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

[0876] [ka]

[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] [ka]

[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] [ka]

[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] [ka]

[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] [ka]

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

[0886] [ka]

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

[0888] [ka]

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

[0890] [ka]

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

[0892] [ka]

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

[0894] [ka]

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

[0896] [ka]

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

[0898] [ka]

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

[0900] [ka]

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

[0902] [ka]

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

[0904] [ka]

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

[0906] [ka]

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

[0908] [ka]

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

[0910] [ka]

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

[0912] [ka]

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

[0914] [ka]

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

[0916] [ka]

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

[0918] [ka]

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

[0920] [ka]

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

[0922] [ka]

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

[0924] [ka]

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

[0926] [ka]

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

[0928] [ka]

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

[0930] [ka]

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

[0932] [ka]

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

[0934] [ka]

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

[0936] [ka]

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

[0938] [ka]

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

[0940] [ka]

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

[0942] [ka]

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

[0944] [ka]

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

[0946] [ka]

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

[0948] [ka]

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

[0950] [ka]

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

[0952] [ka]

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

[0954] [ka]

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

[0956] [ka]

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

[0958] [ka]

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

[0960] [ka]

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

[0962] [ka]

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

[0964] [ka]

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

[0966] [ka]

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

[0968] [ka]

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

[0970] [ka]

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

[0972] [ka]

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

[0974] [ka]

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

[0976] [ka]

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

[0978] [ka]

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

[0980] [ka]

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

[0982] [ka]

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

[0984] [ka]

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

[0986] [ka]

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

[0988] [ka]

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

[0990] [ka]

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

[0992] [ka]

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

[0994] [ka]

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

[0996] [ka]

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

[0998] [ka]

[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 separation and extraction. The organic layer was dried over magnesium sulfate and filtered. The organic layer was then concentrated and the resulting crude product was recrystallized to obtain the target compound (1-1355). EI-MS: m / z=532.

[1000] [ka]

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

[1002] [ka]

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

[1004] [ka]

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

[1006] [ka]

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

[1008] [ka]

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

[1010] [ka]

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

[1012] [ka]

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

[1014] [ka]

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

[1016] [ka]

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

[1018] [ka]

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

[1020] [ka]

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

[1022] [ka]

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

[1024] [ka]

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

[1026] [ka]

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

[1028] [ka]

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

[1030] [ka]

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

[1032] [ka]

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

[1034] [ka]

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

[1036] [ka]

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

[1038] [ka]

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

[1040] [ka]

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

[1042] [ka]

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

[1044] [ka]

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

[1046] [ka]

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

[1048] [ka]

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

[1050] [ka]

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

[1052] [ka]

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

[1054] [ka]

[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 above Synthesis Example (1-56). EI-MS: m / z=588.

[1056] [ka]

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

[1058] [ka]

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

[1060] [ka]

[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 above Synthesis Example (1-56). EI-MS: m / z=631.

[1062] [ka]

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

[1064] [ka]

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

[1066] [ka]

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

[1068] [ka]

[1069] Synthesis Example (2-1): Synthesis of Compound (2-41) [ka] Compound (2-41) was synthesized according to the method described in "Synthesis Example (32)" of WO 2015 / 102118.

[1070] The structure of the compound obtained was confirmed by NMR measurement. 1H-NMR (500MHz, CDCl3): δ=1.47(s,36H), 2.17(s,3H), 5.97(s,2H), 6.68(d,2H), 7.28(d,4H), 7.49(dd,2H), 7.67(d,4H), 8.97(d,2H).

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

[1072] Compound (2-31) was synthesized according to the method described in "Synthesis Example (32)" of WO 2015 / 102118.

[1073] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl3): δ=1.46(s,18H), 1.47(s,18H), 6.14(d,2H), 6.75(d,2H), 7.24(t,1H), 7.29(d,4H), 7.52(dd,2H), 7.67(d,4H), 8.99(d,2H).

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

[1075] Compound (2-46) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[1076] The structure of the compound obtained was confirmed by NMR measurement. 1H-NMR (CDCl3): δ=1.20(s,9H), 1.37(s,18H), 1.46(s,9H), 1.47(s,9H), 2.18(s,3H), 5.97(s,1H), 6.08(d,1H), 6.63(d,1H) ), 6.66(d,1H), 7.20(d,2H), 7.27(d,2H), 7.32(dd,1H), 7.48(dd,1H), 7.61(t,1H), 7.67(d,2H), 8.84(d,1H), 8.94(d,1H).

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

[1078] Compound (2-37) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[1079] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (CDCl3): δ=1.20(s,9H), 1.36(s,18H), 1.46(s,9H), 1.47(s,9H), 6.14(d,1H), 6.25(d,1H), 6.68(d,1H), 6.73 (d,1H), 7.21(d,2H), 7.29(d,3H), 7.34(dd,1H), 7.51(dd,1H), 7.61(t,1H), 7.67(d,2H), 8.86(d,1H), 8.96(d,1H).

[1080] Synthesis Example (2-5): Synthesis of Compound (2-42) [ka]

[1081] The compound represented by formula (2-42) was synthesized in the same manner as in Synthesis Example (2-1).

[1082] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (CDCl3): δ=1.37(s,18H), 1.46(s,9H), 1.47(s,9H), 2.17(s,3H), 5.56(s,1H), 5.99(s,1H), 6.68(d,1H), 6.74(d ,1H), 7.19(d,2H), 7.24~7.29(m,3H), 7.42(t,1H), 7.49(dd,1H), 7.61(t,1H), 7.68(d,2H), 8.91(dd,1H), 8.92(d,1H).

[1083] Synthesis Example (2-6): Synthesis of Compound (2-49) [ka]

[1084] Compound (2-49) was synthesized according to the method described in “Comparative Synthesis Example (1)” of JP-A-2016-88927.

[1085] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (CDCl3): δ=1.33(s,18H), 1.46(s,18H), 5.55(s,2H), 6.75(d,2H), 6.89( t,2H), 6.94(d,4H), 7.06(t,4H), 7.13(d,4H), 7.43~7.46(m,6H), 8.95(d,2H).

[1086] Synthesis Example (2-7): Synthesis of Compound (2-50) [ka]

[1087] Compound (2-50) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[1088] The structure of the compound obtained was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=1.3(s,18H), 1.3(s,18H), 1.5(s,18H), 5.8(s,2H), 6.6( d,2H), 6.8(dd,4H), 7.1(dd,4H), 7.1(dd,4H), 7.4~7.5(m,6H), 8.9(d,2H).

[1089] Synthesis Example (2-8): Synthesis of Compound (2-53) [ka]

[1090] Compound (2-53) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[1091] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (CDCl3): δ=1.35(s,18H), 1.50(s,18H), 6.34(s,2H), 6.85(d,2H), 7.16(t,2H), 7.23(t,2H), 7.32~7.35(m,6H), 7.56(dd,2H), 7.63(d,4H), 7.99(d,2H), 9.05(d,2H).

[1092] Synthesis Example (2-9): Synthesis of Compound (2-33) [ka]

[1093] Compound (2-33) was synthesized according to the method described in "Synthesis Example (32)" of WO 2015 / 102118.

[1094] The structure of the compound obtained was confirmed by NMR measurement. 1H-NMR (CDCl3): δ=1.22(s,9H), 1.37(s,9H), 1.46(s,9H), 1.47(s,9H), 6.14(d,1H), 6.18(d,1H), 6.72(d,1H), 6.74(d,1H), 7.19( ddd,1H), 7.23~7.30(m,3H), 7.34(dd,1H), 7.41(t,1H), 7.51(dd,1H), 7.58~7.64(m,2H), 7.67(d,2H), 8.86(d,1H), 8.96(d,1H).

[1095] Synthesis Example (2-10): Synthesis of Compound (2-508) [ka]

[1096] Under a nitrogen atmosphere, 4-(t-amyl)aniline (15.0 g) was dissolved in acetonitrile (150 ml), and bromine (22.5 g) was added dropwise to the solution under ice cooling and stirred for 0.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene) to obtain intermediate (IA) (20.0 g).

[1097] [ka]

[1098] Under a nitrogen atmosphere, copper chloride (10.1 g) and intermediate (IA) (20.0 g) were dissolved in acetonitrile (100 ml), and t-butyl nitrite (9.6 g) dissolved in acetonitrile (50 ml) was added dropwise at 60°C, followed by stirring at the same temperature for 0.5 hours. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution and stirred. The organic layer was then separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain intermediate (IB) (19.0 g).

[1099] [ka]

[1100] Under a nitrogen atmosphere, intermediate (IB) (10.0 g), bis(4-t-butylphenyl)amine (18.2 g), dichlorobis(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 0.21 g) as a palladium catalyst, sodium t-butoxide (NaOtBu, 7.1 g), and xylene (100 ml) were placed in a flask and heated at 100 °C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred. The organic layer was separated and washed with water. The organic layer was then concentrated to obtain the crude product. The crude product was purified using a silica gel short column (eluent: toluene) to obtain intermediate (IC) (18.0 g).

[1101] [ka]

[1102] A 1.56 M t-butyllithium pentane solution (28.9 ml) was added to a flask containing intermediate (IC) (18.0 g) and t-butylbenzene (500 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 70°C and stirred for 0.5 hours. Components with boiling points lower than t-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (11.3 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (5.8 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and the mixture was separated. The organic layer was concentrated and purified using a silica gel short column (eluent: toluene). The obtained crude product was recrystallized from chlorobenzene to obtain compound (2-508) (7.1 g).

[1103] [ka]

[1104] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (CDCl3): δ=0.49(t,3H), 0.92(s,6H), 1.28(q,2H), 1.46(s,18H), 1.47(s,18 H), 6.05(s,2H), 6.77(d,2H), 7.28(m,4H), 7.50(m,2H), 7.67(m,4H), 8.97(d,2H).

[1105] Synthesis Example (2-11): Synthesis of Compound (2-538) [ka]

[1106] Under a nitrogen atmosphere, 3,4,5-trichloroaniline (12.0 g), d 5 30.0 g of bromobenzene, 0.43 g of dichlorobis(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132) as a palladium catalyst, 14.7 g of sodium t-butoxide (NaOtBu), and 200 mL of xylene were placed in a flask and heated at 120°C for 3 hours. After the reaction, water and ethyl acetate were added to the reaction mixture and stirred. The organic layer was then separated and washed with water. The organic layer was then concentrated to obtain the crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 1 (volume ratio)) to obtain 15.0 g of intermediate (ID).

[1107] [ka]

[1108] Under a nitrogen atmosphere, intermediate (ID) (15.0 g), bis(4-t-butylphenyl)amine (25.9 g), bis(dibenzylideneacetone)palladium (0.48 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.86 g), sodium t-butoxide (10.0 g), and xylene (130 mL) were placed in a flask and heated to 100 °C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred. The organic layer was separated and washed with water. The organic layer was then concentrated to obtain the crude product. The crude product was pur...

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, as a host material, an anthracene-based compound represented by the following formula (1), and, as a dopant material, a polycyclic aromatic compound represented by the following formula (2) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2): 【Chemical 1】 (In formula (1), Ar ｃ is an optionally substituted aryl or an 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 atom in the compound represented by formula (1) may be substituted with a halogen atom, a cyano atom, or a deuterium atom. (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 atom in these rings may be substituted; X １ and X ２ are each independently >O, >N-R, >C(-R) ２ , >S, or >Se, and R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the >C(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >N-R and / or the >C(-R) ２ R may be bonded to the ring A, ring B, and / or ring C via a linking group or a single bond, In the compound represented by formula (2) or a multimer thereof, at least one of the aryl ring and the heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen atom in the cycloalkane may be substituted, and at least one —CH ２ - may be replaced by -O-, At least one hydrogen atom in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or halogen.

2. The organic electroluminescent device according to claim 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 the 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); 【Chemistry 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, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen 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 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (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 atom in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; X Ｘ are each independently >O, >S, >N—R, or >C(—R) ２ wherein R in the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; and wherein the >C(-R) ２ R's are each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally 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, and R of the >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 the >C(-R) ２ R 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 R in the >N-R and / or the >C(-R) ２ R is -O-, -S-, -C(-R) ２ may be bonded to the ring a, ring b, and / or ring c via a single bond, and the -C(-R) ２ Each R in - is 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 a multimer thereof, at least one of the aryl ring and the heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen atom in the cycloalkane may be substituted, and at least one —CH ２ - may be replaced by -O-, At least one hydrogen atom 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 polymer, 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 organic electroluminescent device according to claim 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).

4. The organic electroluminescent device according to claim 3, wherein the compound represented by formula (2) is any one of compounds represented by the following formulas: 【Chemistry 3】 【Chemistry 4】 【Chemistry 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 any two of the above are 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.

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): 【Chemistry 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 each independently represents phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), in which at least one hydrogen atom 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), in which when two hydrogen atoms of methylene in fluorenyl and benzofluorenyl are both 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 A carbon atom on the anthracene ring to which ' is not bonded may have a methyl or t-butyl bonded instead of a hydrogen atom, At least one hydrogen atom in the compound represented by formula (1A), (1B), (1C), (1D) or (1E) may be substituted with a halogen atom, a cyano atom or a deuterium atom; The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position, In formula (A), Y is —O—, —S— or >N—R ３９ and 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; R ２１ ~R ２８ adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen atom 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; R ３９ is hydrogen or optionally substituted aryl.

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 formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any position in each of formulae (A-1) to (A-14), and * indicates the position, In formulas (A-1) to (A-14), Y is —O—, —S—, or >N—R ３９ and R ３９ represents hydrogen or aryl, and at least one hydrogen in the groups 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; The organic electroluminescent device according to claim 6 . 【Chemistry 7】

8. Ar ｃ ', Ar １１ ', Ar １２ ', Ar １３ ', Ar １４ ', Ar １５ ', Ar １７ ', and Ar １８ each independently represents 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 atom in these groups may be substituted by phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of formulas (A-1) to (A-4), At least one hydrogen atom 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 optionally substituted aryl or optionally substituted heteroaryl, and Ar １１ , Ar １２ , Ar １３ , Ar １６ , Ar １７ and Ar １８ The organic electroluminescent device according to claim 5 , wherein each of

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 device according to claim 9 , wherein at least one selected from the group consisting of: 【Chemistry 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; R ２１ ~R ２８ Adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen atom 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. 10. The organic electroluminescent device according to claim 9, wherein at least one hydrogen atom in the compound represented by formula (1) is substituted with deuterium.

13. 13. The organic electroluminescent device according to claim 1, further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein 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, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

14. 14. The organic electroluminescent device according to claim 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 device according to any one of claims 1 to 14.

16. A lighting device comprising the organic electroluminescent device according to any one of claims 1 to 14.

17. An anthracene-based compound represented by the following formula (1): 【Chemistry 9】 In formula (1), Ar ｃ is an optionally substituted aryl or an 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 atom in the compound represented by formula (1) may be substituted with a halogen atom, a cyano atom, or a deuterium atom.

18. The anthracene compound according to claim 17, represented by the following formula (1Aa): 【Chemistry 10】 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 atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-14), and when hydrogen atoms of methylene groups in fluorenyl and benzofluorenyl are both substituted with phenyl, these phenyls may be bonded to each other via a single bond, and Ar ｃ ', Ar １４ ', or Ar １５ A carbon atom on the anthracene ring to which ' is not bonded may have a methyl or t-butyl bonded instead of a hydrogen atom, At least one hydrogen atom in the compound represented by formula (1Aa) may be substituted with a halogen atom, a cyano group, or a deuterium group; The groups represented by formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any position in each of formulae (A-1) to (A-14), and * indicates the position, In formulas (A-1) to (A-14), Y is —O—, —S—, or >N—R ３９ and R ３９ represents hydrogen or aryl, and at least one hydrogen in the groups 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; However, at least one hydrogen atom in the compound represented by formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen atom in the compound represented by formula (1Aa) is substituted with deuterium.

19. Ar ｃ’ , Ar １４ ' and Ar １５ ' each independently represent 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 atom 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 compound according to claim 18.

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

21. The anthracene compound according to claim 18, which is represented by any one of the following formulas: 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 (In the above formula, D represents deuterium.)

22. The anthracene compound according to claim 17, represented by any one of the following formulas: 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 (In the above formula, D represents deuterium.)

23. The anthracene compound according to claim 17, represented by any one of the following formulas: 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】

24. The anthracene compound according to claim 17, represented by any one of the following formulas: 【Chemical 26】 【Chemical 27】 【Chemical 28】 【Chemical 29】 (In the above formula, D represents deuterium.)

25. The anthracene compound according to claim 17, represented by any one of the following formulas: 【Chemistry 30】 【Chemical 31】 (In the above formula, D represents deuterium.)

26. The anthracene compound according to claim 17, represented by any one of the following formulas: 【Chemical 32】 (In the above formula, Me represents methyl, tBu represents t-butyl, and CyHex represents cyclohexyl.)

27. The anthracene compound according to claim 17, represented by any one of the following formulas: 【Chemical 33】 【Chemical 34】 (In the above formula, D represents deuterium.)

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