Cyclic azine compound, material for organic electroluminescent device, electron transport material for organic electroluminescent device, and organic electroluminescent device

Abstract

To provide a cyclic azine compound having excellent current efficiency and a long service life.SOLUTION: A cyclic azine compound has a specific structure with an aromatic ring and a heterocycle bound to triazine.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to a cyclic azine compound, a material for an organic electroluminescent device, an electron transport material for an organic electroluminescent device, and an organic electroluminescent device. [Background technology]

[0002] Organic electroluminescent devices are used not only for small displays but also for large televisions, lighting, and the like, and their development is being actively pursued. For example, Patent Document 1 discloses a cyclic azine compound having a specific substituent, which is useful as a material for organic electroluminescent devices and contributes to the provision of organic electroluminescent devices having excellent heat resistance, reduced driving voltage, and long life. Patent Document 2 discloses a cyclic azine compound having a diarylpyridine structure. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2011-063584 A [Patent Document 2] International Publication No. 2017 / 221974 Summary of the Invention [Problem to be solved by the invention]

[0004] However, in recent years, market demands for organic electroluminescent devices have become increasingly high, and materials that are excellent in all respects of current efficiency characteristics, driving voltage characteristics, and long life characteristics are being sought. Here, although the organic electroluminescent devices using the cyclic azine compounds disclosed in Patent Documents 1 and 2 exhibit excellent driving voltage characteristics, further improvements are required in terms of the life span and current efficiency of the device.

[0005] One aspect of the present invention is directed to providing a cyclic azine compound, a material for an organic electroluminescent device, and an electron transport material for an organic electroluminescent device, which are excellent in durability and current efficiency. Another aspect of the present invention is to provide an organic electroluminescent device having excellent durability and current efficiency. [Means for solving the problem]

[0006] The cyclic azine compound according to one embodiment of the present invention is represented by formula (1):

[0007] [ka]

[0008] In formula (1), Ar 1 , and Ar 2 each independently represents a phenyl group, a biphenyl group, or a naphthyl group; X 1 ~X 5 are each independently C-Ar 3 , CR, or a nitrogen atom; X 1 ~X 5 one or two of the are nitrogen atoms; X 1 ~X 5 One or two of the C-Ar 3 is; Ar 3 teeth, a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked; (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings, or (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) a group formed by a combination of any two or more selected from (i) to (iii) above; Ar3 The total number of ring-constituting carbon atoms is 4 to 25; R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; L 1 represents a phenylene group or a single bond; n 1 represents 0, 1, or 2; X 1 ~X 5 Among them, only one is C-Ar 3 and X 1 , and X 5 Either one of them is C-Ar 3 If so, L 1 is a single bond, n 1 is 0 or 1; X 1 ~X 5 Among them, only one is C-Ar 3 and X 2 ,X 3 , and X 4 One of the following is C-Ar 3 If so, L 1 is a phenylene group or a single bond, n 1 is 0, 1, or 2; X 1 ~X 5 Among them, two are C-Ar 3 If so, X 1 ,X 3 , and X 5 Of these, one is a nitrogen atom and the other two are CR. X 2 , and X 4 C-Ar 3 and L 1 is a phenylene group or a single bond, n 1 is 1 or 2; The two CRs and the two C-Ars 3 may be the same or different; Ar 1 , Ar 2 , and Ar 3 Each group represented by the formula (I) may independently have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0009] A material for an organic electroluminescent device according to another embodiment of the present invention contains the above cyclic azine compound. An organic electroluminescent device according to another embodiment of the present invention comprises the above cyclic azine compound. Effect of the Invention

[0010] According to one aspect of the present invention, it is possible to provide a cyclic azine compound, a material for an organic electroluminescence device, and an electron transport material for an organic electroluminescence device, which are excellent in durability and current efficiency. According to another aspect of the present invention, it is possible to provide an organic electroluminescent device having excellent durability and current efficiency. [Brief description of the drawings]

[0011] [Figure 1] 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent device containing a cyclic azine compound according to one embodiment of the present invention. [Diagram 2] FIG. 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent device containing a cyclic azine compound according to one embodiment of the present invention (Device Example 1). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Hereinafter, a cyclic azine compound according to one embodiment of the present invention will be described in detail.

[0013] <Cyclic azine compounds> The cyclic azine compound according to one embodiment of the present invention is represented by formula (1):

[0014] [ka]

[0015] In formula (1), Ar 1 , and Ar 2 each independently represents a phenyl group, a biphenyl group, or a naphthyl group; X 1 ~X 5 are each independently C-Ar 3 , CR, or a nitrogen atom; X 1 ~X 5 one or two of the are nitrogen atoms; X 1 ~X 5 One or two of the C-Ar 3 is; Ar 3 teeth, a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked; (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings, or (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) a group formed by a combination of any two or more selected from (i) to (iii) above; Ar 3 The total number of ring-constituting carbon atoms is 4 to 25; R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; L 1 represents a phenylene group or a single bond; n 1 represents 0, 1, or 2; X 1 ~X 5 Among them, only one is C-Ar 3 and X 1 , and X 5 Either one of them is C-Ar 3If so, L 1 is a single bond; n 1 is 0 or 1; X 1 ~X 5 Among them, only one is C-Ar 3 and X 2 ,X 3 , and X 4 One of the following is C-Ar 3 If so, L 1 is a phenylene group or a single bond, n 1 is 0, 1, or 2; X 1 ~X 5 Among them, two are C-Ar 3 If so, X 1 ,X 3 , and X 5 Of these, one is a nitrogen atom and the other two are CR. X 2 , and X 4 C-Ar 3 and L 1 is a phenylene group or a single bond; n 1 is 1 or 2; The two CRs and the two C-Ars 3 may be the same or different; Ar 1 , Ar 2 , and Ar 3 Each group represented by the formula (I) may independently have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0016] The cyclic azine compound according to one embodiment of the present invention is more preferably represented by formula (11) or formula (21):

[0017] [ka]

[0018] In formula (11), Ar 11 , and Ar 12 each independently represents a phenyl group or a naphthyl group; Ar 13 , and Ar 14 are each independently a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked; (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings, or (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) a group formed by a combination of any two or more selected from (i) to (iii) above; Ar 13 , and Ar 14 The total number of ring-constituting carbon atoms is 4 to 25; L 11 represents a phenylene group or a single bond; Z 11 and Z 12 one of them represents a nitrogen atom and the other represents CH; n 11 is either 1 or 2. Ar 11 ~Ar 14 Each group represented by the formula (I) may independently have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0019] Ar 11 , and Ar 12 are each independently a phenyl group or a naphthyl group; Ar11 , and Ar 12 When each group represented by the formula: is a phenyl group, the phenyl group may each independently have a phenyl group.

[0020] [ka]

[0021] In formula (21), Ar 21 , and Ar 22 each independently represents a phenyl group, a biphenyl group, or a naphthyl group; X 21 ~X 25 are each independently C-Ar 23 , CR, or a nitrogen atom; X 21 ~X 25 Among these, one or two are nitrogen atoms; Ar 23 teeth, a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked; (i) an aromatic hydrocarbon group having 6 to 18 carbon atoms, (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings, or (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) a group consisting of any two or more selected from (i) to (iii); Ar 23 The total number of ring-constituting carbon atoms is 4 to 25; R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; X 21 ~X 25 Only one of the C-Ar 23 is; X 21 ~X 25 Among them, X 21 and X 25 Either one of them is C-Ar 23If so, L 21 is a single bond, n 21 is 0 or 1; X 21 ~X 25 Of these, X 22 ~X 24 One of the following is C-Ar 23 If so, L 21 is a phenylene group or a single bond, n 21 is 0, 1, or 2; Ar 21 ~Ar 23 Each group represented by the formula: may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group.

[0022] Hereinafter, the cyclic azine compounds represented by formula (1), formula (11), and formula (21) may be referred to as cyclic azine compounds (1), (11), and (21), respectively. Definitions of the substituents in the cyclic azine compounds (1), (11), and (21), and preferred specific examples thereof, are as follows:

[0023] [Ar 1 , Ar 2 About In formula (1), Ar 1 , and Ar 2 each independently represents a phenyl group, a biphenyl group, or a naphthyl group, and each independently may have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. Ar 1 , and Ar 2 and are each independently more preferably a phenyl group, a naphthyl group, or a phenyl group having a phenyl group (that is, a biphenyl group), in terms of excellent electron transporting material properties.

[0024] [X1 ~X 5 , Ar 3 , Regarding R] X 1 ~X 5 are each independently C-Ar 3 , CR, or a nitrogen atom. X 1 ~X 5 One or two of the groups are nitrogen atoms. X 1 ~X 5 One or two of the C-Ar 3 It is.

[0025] Ar 3 teeth, a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked; (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings, or (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) A group formed by combining any two or more selected from the above (i) to (iii). Ar 3 Each of the groups (i) to (iv) represented by the following formula may independently have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. 3 It is more preferable that the compound has no substituent in terms of ease of synthesis.

[0026] The aromatic hydrocarbon group (i) is not particularly limited, and preferred examples thereof include a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a triphenylenyl group, a chrysenyl group, a perylenyl group, a fluoranthenyl group, an acenaphthyl group, etc. As described above, these substituents (aromatic hydrocarbon groups) may each independently have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0027] The nitrogen-containing heteroaromatic group (ii) is not particularly limited, but preferred examples include pyridyl, pyrazyl, pyrimidyl, pyridazyl, quinolyl, isoquinolyl, phenanthridyl, benzoquinolyl, and acridinyl. Heteroaromatic groups containing a 5-membered ring (e.g., carbazolyl) are not included in the nitrogen-containing heteroaromatic group (ii), and are not included in the cyclic azine compound represented by formula (1). As described above, these substituents (nitrogen-containing heteroaromatic groups) may each independently have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0028] The heteroaromatic group of (iii) is not particularly limited, and preferred examples thereof include a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, a dibenzofuryl group, etc. As described above, these substituents (heteroaromatic groups) may each independently have one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0029] Ar3 The alkyl group having 1 to 4 carbon atoms in is not particularly limited, but preferred examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and a t-butyl group.

[0030] Ar 3 In the above, the alkoxy group having 1 to 4 carbon atoms is not particularly limited, but preferred examples include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a t-butoxy group.

[0031] Specifically, Ar 3 is preferably a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, an acenaphthyl group, a pyrimidyl group, a pyrazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group, each of which may be substituted with one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. 3 is more preferably a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, an acenaphthyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group, which optionally have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. In formula (1), Ar 3 If two occur, two Ar 3 may be the same as or different from each other.

[0032] Ar 3 The total number of ring-constituting carbon atoms of the group represented by the formula: is 4 to 25. In addition, Ar 3 When Ar has a substituent, the number of carbon atoms of the substituent is 3 Therefore, for example, Ar 3 is a fluorene group (ring carbon number 13), and Ar 3 When the group represented by the formula (I) has a phenyl group, the fluorene group having a phenyl group is 3 ) totaling 19 ring carbon atoms. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0033] [L 1 About L 1 represents a phenylene group or a single bond.

[0034] [n 1 About n 1 represents 0, 1, or 2.

[0035] X is favored because of the ease of obtaining raw materials. 1 ~X 5 It is preferred that only one of is a nitrogen atom.

[0036] X 1 ~X 5 Among them, only one is C-Ar 3 and X 1 , and X 5 Either one of them is C-Ar 3 If so, L 1 is a single bond, n 1 is either 0 or 1. X 1 ~X 5 Among them, only one is C-Ar 3 and X 2 ,X 3 , and X 4 One of the following is C-Ar 3 If so, L1 is a phenylene group or a single bond, n 1 is 0, 1, or 2. X 1 ~X 5 Among them, two are C-Ar 3 If so, X 1 ,X 3 , and X 5 Of these, one is a nitrogen atom and the other two are CR. X 2 , and X 4 C-Ar 3 and L 1 is a phenylene group or a single bond, n 1 is 1 or 2. The two CRs and the two C-Ars 3 may be the same or different.

[0037] [Ar 11 , Ar 12 About In formula (11), Ar 11 , and Ar 12 each independently represents a phenyl group or a naphthyl group, and each independently may have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. Ar 11 , and Ar 12 and are each independently more preferably a phenyl group, a naphthyl group, or a phenyl group having a phenyl group (that is, a biphenyl group), in terms of excellent electron transporting material properties.

[0038] [Ar 13 , Ar 14 About In formula (11) and formula (1), Ar 13 , and Ar 14 are each independently (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms which is an optionally linked monocyclic ring, an optionally linked condensed ring, or a structure in which these are linked; (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting of only 6-membered rings, which is an optionally linked monocyclic ring, an optionally linked condensed ring, or a structure in which these are linked; (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, which is an optionally linked monocyclic ring, an optionally linked condensed ring, or a structure in which these are linked; (iv) A group formed by combining any two or more selected from the above (i) to (iii). Ar 13 , and Ar 14 Each of the groups (i) to (iv) represented by the following formula may independently have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. 13 , and Ar 14 It is more preferable that the group has no substituent.

[0039] The aromatic hydrocarbon group (i) is not particularly limited, and preferred examples thereof include a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a triphenylenyl group, a chrysenyl group, a perylenyl group, a fluoranthenyl group, an acenaphthyl group, etc. As described above, these substituents (aromatic hydrocarbon groups) may each independently have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0040] The nitrogen-containing heteroaromatic group (ii) is not particularly limited, but preferred examples include pyridyl, pyrazyl, pyrimidyl, pyridazyl, quinolyl, isoquinolyl, phenanthridyl, benzoquinolyl, and acridinyl. Heteroaromatic groups containing a 5-membered ring (e.g., carbazolyl) are not included in the nitrogen-containing heteroaromatic group (ii), and are not included in the cyclic azine compounds represented by formula (11) and formula (1). As described above, these substituents (nitrogen-containing heteroaromatic groups) may each independently have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0041] The heteroaromatic group of (iii) is not particularly limited, but preferred examples include a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, a dibenzofuryl group, etc. As described above, these substituents (heteroaromatic groups) may each independently have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0042] Ar 13 , and Ar 14 The alkyl group having 1 to 4 carbon atoms in is not particularly limited, but preferred examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and a t-butyl group.

[0043] Ar 13 , and Ar 14 In the above, the alkoxy group having 1 to 4 carbon atoms is not particularly limited, but preferred examples include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a t-butoxy group.

[0044] Specifically, Ar 13 , and Ar 14 are each independently preferably a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, an acenaphthyl group, a pyrimidyl group, a pyrazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group, each of which may be substituted with one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. 13 , and Ar 14 is more preferably a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrimidyl group, a pyrazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a biphenyl group, or a pyridylphenyl group.

[0045] Ar 13 , and Ar 14 Specific examples of the group represented by the formula: is not particularly limited, but preferred examples include the groups (1) to (44) shown below.

[0046] (1): Phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, 4-propylphenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3- Isopropylphenyl group, 4-isopropylphenyl group, 2,4-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2-butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2,4-dibutylphenyl group, 3,5-dibutylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2,4-di-tert-butylphenyl group, and 3,5-di-tert-butylphenyl group.

[0047] (2): biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl-2-yl group, 4'-methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group, 3-ethyl and 5-tert-butylbiphenyl-2-yl group.

[0048] (3): 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 2-methylpyridin-5-yl group, 2-methylpyridin-6-yl group, 3-methylpyridin-2-yl group, 3-methylpyridin-4-yl group, 3-methylpyridin-5-yl group, 3-methylpyridin-6-yl group, 4-methylpyridin-2-yl group, 4-methylpyridin-3-yl group, 2,6-dimethylpyridin-3-yl group, 2,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-2-yl group, 3,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-5-yl group.

[0049] (4): 2-phenylpyridin-6-yl group, 3-phenylpyridin-6-yl group, 4-phenylpyridin-6-yl group, 5-phenylpyridin-6-yl group, 2-phenylpyridin-3-yl group, 2-phenylpyridin-5-yl group, 3-phenylpyridin-5-yl group, 4-phenylpyridin-3-yl group, 3-phenylpyridin-4-yl group, 2-phenylpyridin-4-yl group, 2-(2-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, phenyl group, 4-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(3-methyl-2-pyridyl)phenyl group, 3-(3-methyl-2-pyridyl)phenyl group, 4-(3-methyl-2-pyridyl)phenyl group, 2-(4-methyl-2-pyridyl)phenyl group, 3-(4-methyl-2-pyridyl)phenyl group, 4-(4-methyl-2-pyridyl)phenyl group, 2-(5-methyl-2-pyridyl)phenyl group, 3-(5-methyl-2-pyridyl)phenyl group, 4-(5-methyl-2-pyridyl)phenyl group, 2-(6-methyl-2-pyridyl)phenyl group, 3-(6-methyl-2-pyridyl)phenyl group, 4-(6-methyl-2-pyridyl)phenyl group, 2-(2-methyl-3-pyridyl)phenyl group, 3-(2-methyl-3-pyridyl)phenyl group, 4-(2-methyl-3-pyridyl)phenyl group, 2-(4-methyl-3-pyridyl)phenyl group, 3-(4-methyl-3-pyridyl)phenyl group, 4-(4-methyl-3-pyridyl)phenyl group, 2-(5-methyl-3-pyridyl)phenyl group, 3-(5-methyl-3-pyridyl)phenyl group, phenyl group, 4-(5-methyl-3-pyridyl)phenyl group, 2-(6-methyl-3-pyridyl)phenyl group, 3-(6-methyl-3-pyridyl)phenyl group, 4-(6-methyl-3-pyridyl)phenyl group, 2-(2-methyl-4-pyridyl)phenyl group, 3-(2-methyl-4-pyridyl)phenyl group, 4-(2-methyl-4-pyridyl)phenyl group, 2-(3-methyl-4-pyridyl)phenyl group, 3-(3-methyl-4-pyridyl)phenyl group, 4-(3-methyl-4-pyridyl)phenyl group, 2,6-diphenylpyridin-3-yl group, 2,6-diphenylpyridin-4-yl group, 4,6-diphenylpyridin-2-yl group, 3,6-diphenylpyridin-4-yl group, 3,6-diphenylpyridin-5-yl group.

[0050] (5): 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalen-4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalen-1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2- Phenylnaphthalen-7-yl group, 2-phenylnaphthalen-8-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalen-7-yl group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalen-5-yl group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-8-yl group.

[0051] (6): 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-phenylphenanthrene-2-yl group, 1-phenylphenanthrene-3-yl group, 1-phenylphenanthrene-4-yl group, 1-phenylphenanthrene-5-yl group, 1-phenylphenanthrene-6-yl group, 1-phenylphenanthrene-7-yl group, 1-phenylphenanthrene-8-yl group, 1-phenylphenanthrene-9-yl group, 1-phenylphenanthrene-10-yl group, 2-phenylphenanthrene group, anthren-1-yl group, 2-phenylphenanthrene-3-yl group, 2-phenylphenanthrene-4-yl group, 2-phenylphenanthrene-5-yl group, 2-phenylphenanthrene-6-yl group, 2-phenylphenanthrene-7-yl group, 2-phenylphenanthrene-8-yl group, 2-phenylphenanthrene-9-yl group, 2-phenylphenanthrene-10-yl group, 3-phenylphenanthrene-1-yl group, 3-phenylphenanthrene-2-yl group, 3-phenylphenanthrene-4-yl group, 3-phenylphenanthrene-5 -yl group, 3-phenylphenanthren-6-yl group, 3-phenylphenanthren-7-yl group, 3-phenylphenanthren-8-yl group, 3-phenylphenanthren-9-yl group, 3-phenylphenanthren-10-yl group, 4-phenylphenanthren-1-yl group, 4-phenylphenanthren-2-yl group, 4-phenylphenanthren-3-yl group, 4-phenylphenanthren-5-yl group, 4-phenylphenanthren-6-yl group, 4-phenylphenanthren-7-yl group, 4-phenylphenanthren-8-yl group, 4- phenylphenanthrene-9-yl group, 4-phenylphenanthrene-10-yl group, 1-methylphenanthrene-2-yl group, 1-methylphenanthrene-3-yl group, 1-methylphenanthrene-4-yl group, 1-methylphenanthrene-5-yl group, 1-methylphenanthrene-6-yl group, 1-methylphenanthrene-7-yl group, 1-methylphenanthrene-8-yl group, 1-methylphenanthrene-9-yl group, 1-methylphenanthrene-10-yl group, 2-methylphenanthrene-1-yl group, 2-methylphenanthrene-3-yl group,2-methylphenanthren-4-yl group, 2-methylphenanthren-5-yl group, 2-methylphenanthren-6-yl group, 2-methylphenanthren-7-yl group, 2-methylphenanthren-8-yl group, 2-methylphenanthren-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methylphenanthren-2-yl group, 3-methylphenanthren-4-yl group, 3-methylphenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren phenanthrene-7-yl group, 3-methylphenanthrene-8-yl group, 3-methylphenanthrene-9-yl group, 3-methylphenanthrene-10-yl group, 4-methylphenanthrene-1-yl group, 4-methylphenanthrene-2-yl group, 4-methylphenanthrene-3-yl group, 4-methylphenanthrene-5-yl group, 4-methylphenanthrene-6-yl group, 4-methylphenanthrene-7-yl group, 4-methylphenanthrene-8-yl group, 4-methylphenanthrene-9-yl group, 4-methylphenanthrene-10-yl group.

[0052] (7): 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenylanthracen-2-yl group, 1-phenylanthracen-3-yl group, 1-phenylanthracen-4-yl group, 1-phenylanthracen-5-yl group, 1-phenylanthracen-6-yl group, 1-phenylanthracen-7-yl group, 1-phenylanthracen-8-yl group, 1-phenylanthracen-9-yl group, 1-phenylanthracen-10-yl group, 2-phenylanthracen-1-yl group, 2-phenylanthracen-3-yl group, 2-phenylanthracen-4-yl group, 2-phenylanthracen -5-yl group, 2-phenylanthracen-6-yl group, 2-phenylanthracen-7-yl group, 2-phenylanthracen-8-yl group, 2-phenylanthracen-9-yl group, 2-phenylanthracen-10-yl group, 9-phenylanthracen-1-yl group, 9-phenylanthracen-2-yl group, 9-phenylanthracen-3-yl group, 9-phenylanthracen-4-yl group, 9-phenylanthracen-5-yl group, 9-(2-pyridyl)-anthracen-10-yl group, 9-(3-pyridyl)-anthracen-10-yl group, and 9-(4-pyridyl)-anthracen-10-yl group.

[0053] (8): 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-phenylpyren-2-yl group, 1-phenylpyren-3-yl group, 1-phenylpyren-4-yl group, 1-phenylpyren-5-yl group, 1-phenylpyren-6-yl group, 1-phenylpyren-7-yl group, 1-phenylpyren-8-yl group, 1-phenylpyren-9-yl group, 1-phenylpyren-10-yl group, 2-phenylpyren-1-yl group, 2-phenylpyren-3-yl group, 2-phenylpyren-4-yl group, yl group, 2-phenylpyren-5-yl group, 2-phenylpyren-6-yl group, 2-phenylpyren-7-yl group, 2-phenylpyren-8-yl group, 2-phenylpyren-9-yl group, 2-phenylpyren-10-yl group, 9-phenylpyren-1-yl group, 9-phenylpyren-2-yl group, 9-phenylpyren-3-yl group, 9-phenylpyren-4-yl group, 9-phenylpyren-5-yl group, 9-phenylpyren-6-yl group, 9-phenylpyren-7-yl group, 9 ... 1-methylpyren-8-yl group, 9-phenylpyren-10-yl group, 1-methylpyren-2-yl group, 1-methylpyren-3-yl group, 1-methylpyren-4-yl group, 1-methylpyren-5-yl group, 1-methylpyren-6-yl group, 1-methylpyren-7-yl group, 1-methylpyren-8-yl group, 1-methylpyren-9-yl group, 1-methylpyren-10-yl group, 2-methylpyren-1-yl group, 2-methylpyren-3-yl group, 2-methylpyren-4-yl group, 2-methylpyren- 5-yl group, 2-methylpyren-6-yl group, 2-methylpyren-7-yl group, 2-methylpyren-8-yl group, 2-methylpyren-9-yl group, 2-methylpyren-10-yl group, 9-methylpyren-1-yl group, 9-methylpyren-2-yl group, 9-methylpyren-3-yl group, 9-methylpyren-4-yl group, 9-methylpyren-5-yl group, 9-methylpyren-6-yl group, 9-methylpyren-7-yl group, 9-methylpyren-8-yl group, and 9-methylpyren-10-yl group.

[0054] (9): fluoranthene-1-yl group, fluoranthene-1-yl group, fluoranthene-2-yl group, fluoranthene-3-yl group, fluoranthene-4-yl group, fluoranthene-5-yl group, fluoranthene-6-yl group, fluoranthene-7-yl group, fluoranthene-8-yl group, fluoranthene-9-yl group, and fluoranthene-10-yl group.

[0055] (10): triphenylene-1-yl group, triphenylene-2-yl group, acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5-yl group, and chrysen-6-yl group.

[0056] (11): 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, quinoxalin-2-yl group, quinoxalin-5-yl group, quinoxalin-6-yl group, quinazolin-2-yl group, quinazolin-4-yl group group, quinazolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-8-yl group, pyrazin-2-yl group, 5-methylpyrazin-2-yl group, 5,6-diphenylpyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, 2,4-diphenylpyrimidin-6-yl group, 4,6-diphenylpyrimidin-2-yl group, acridine-1-yl group, acridine -1-yl group, acridine-2-yl group, acridine-3-yl group, acridine-4-yl group, acridine-9-yl group, phenanthridin-1-yl group, phenanthridin-1-yl group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridin-4-yl group, phenanthridin-6-yl group, phenanthridin-7-yl group, phenanthridin-8-yl group, phenanthridin-9 ... anthridin-10-yl group, phenazin-1-yl group, phenazin-2-yl group, benzo[h]quinolin-2-yl group, benzo[h]quinolin-3-yl group, benzo[h]quinolin-4-yl group, benzo[h]quinolin-5-yl group, benzo[h]quinolin-6-yl group, benzo[h]quinolin-7-yl group, benzo[h]quinolin-8-yl group, benzo[h]quinolin-9-yl group, benzo[h]quinolin-10-yl group.

[0057] (12): 2-thienyl group, 3-thienyl group, 2-furyl group, 3-furyl group, benzothiophen-2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group, benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group, dibenzothiophen-1-yl group, dibenzothiophen-2-yl group, dibenzothiof and 5-methylthiophen-3-yl group.

[0058] (13): 3-methylbenzothiophene-2-yl group, 4-methylbenzothiophene-2-yl group, 5-methylbenzothiophene-2-yl group, 6-methylbenzothiophene-2-yl group, 7-methylbenzothiophene-2-yl group, 2-methylbenzothiophene-3-yl group, 4-methylbenzothiophene-3-yl group, 5-methylbenzothiophene-3-yl group, 6-methylbenzothiophene-3-yl group, 7-methylbenzothiophene-3-yl group, 2-methylbenzothiophene-4-yl group, 3-methylbenzothiophene-4-yl group, 5-methylbenzothiophene-4-yl group, 6-methylbenzothiophene-4-yl group, 7-methylbenzothiophene-4-yl group a 2-methylbenzothiophen-5-yl group, a 3-methylbenzothiophen-5-yl group, a 4-methylbenzothiophen-5-yl group, a 6-methylbenzothiophen-5-yl group, a 7-methylbenzothiophen-5-yl group, a 2-methylbenzothiophen-6-yl group, a 3-methylbenzothiophen-6-yl group, a 4-methylbenzothiophen-6-yl group, a 5-methylbenzothiophen-6-yl group, a 7-methylbenzothiophen-6-yl group, a 2-methylbenzothiophen-7-yl group, a 3-methylbenzothiophen-7-yl group, a 4-methylbenzothiophen-7-yl group, a 5-methylbenzothiophen-7-yl group, and a 6-methylbenzothiophen-7-yl group.

[0059] (14): 3-methylbenzofuran-2-yl group, 4-methylbenzofuran-2-yl group, 5-methylbenzofuran-2-yl group, 6-methylbenzofuran-2-yl group, 7-methylbenzofuran-2-yl group, 2-methylbenzofuran-3-yl group, 4-methylbenzofuran-3-yl group, 5-methylbenzofuran-3-yl group, 6-methylbenzofuran-3-yl group, 7-methylbenzofuran-3-yl group, 2-methylbenzofuran-4-yl group, 3-methylbenzofuran-4-yl group, 5-methylbenzofuran-4-yl group, 6-methylbenzofuran-4-yl group, 7-methylbenzofuran-4-yl group benzofuran-5-yl group, 2-methylbenzofuran-5-yl group, 3-methylbenzofuran-5-yl group, 4-methylbenzofuran-5-yl group, 6-methylbenzofuran-5-yl group, 7-methylbenzofuran-5-yl group, 2-methylbenzofuran-6-yl group, 3-methylbenzofuran-6-yl group, 4-methylbenzofuran-6-yl group, 5-methylbenzofuran-6-yl group, 7-methylbenzofuran-6-yl group, 2-methylbenzofuran-7-yl group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methylbenzofuran-7-yl group, 6-methylbenzofuran-7-yl group.

[0060] (15): 2-methyldibenzothiophene-1-yl group, 3-methyldibenzothiophene-1-yl group, 4-methyldibenzothiophene-1-yl group, 6-methyldibenzothiophene-1-yl group, 7-methyldibenzothiophene-1-yl group, 8-methyldibenzothiophene-1-yl group, 9-methyldibenzothiophene-1-yl group, 1-methyldibenzothiophene-2-yl group, 3-methyldibenzothiophene-2-yl group, 4-methyldibenzothiophene-2 ​​... dibenzothiophen-2-yl group, 7-methyldibenzothiophen-2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyldibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group, 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothiophen-3-yl group, and 9-methyldibenzothiophen-3-yl group.

[0061] (16): 2-methyldibenzofuran-1-yl group, 3-methyldibenzofuran-1-yl group, 4-methyldibenzofuran-1-yl group, 6-methyldibenzofuran-1-yl group, 7-methyldibenzofuran-1-yl group, 8-methyldibenzofuran-1-yl group, 9-methyldibenzofuran-1-yl group, 1-methyldibenzofuran-2-yl group, 3-methyldibenzofuran-2-yl group, 4-methyldibenzofuran-2 ... dibenzofuran-2-yl group, 7-methyldibenzofuran-2-yl group, 8-methyldibenzofuran-2-yl group, 9-methyldibenzofuran-2-yl group, 1-methyldibenzofuran-3-yl group, 2-methyldibenzofuran-3-yl group, 4-methyldibenzofuran-3-yl group, 6-methyldibenzofuran-3-yl group, 7-methyldibenzofuran-3-yl group, 8-methyldibenzofuran-3-yl group, 9-methyldibenzofuran-3-yl group.

[0062] (17): 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenylthiophen-3-yl group, 4-phenylthiophen-3-yl group, and 5-phenylthiophen-3-yl group.

[0063] (18): 3-phenylfuran-2-yl group, 4-phenylfuran-2-yl group, 5-phenylfuran-2-yl group, 2-phenylfuran-3-yl group, 4-phenylfuran-3-yl group, and 5-phenylfuran-3-yl group.

[0064] (19): 3-phenylbenzothiophen-2-yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7-phenylbenzothiophen-2-yl group, 2-phenylbenzothiophen-3-yl group, 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophen-3-yl group, 7-phenylbenzothiophen-3-yl group, 2-phenylbenzothiophen-4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenylbenzothiophen-4-yl group, 7-phenylbenzothiophen-4-yl group a 2-phenylbenzothiophen-5-yl group, a 3-phenylbenzothiophen-5-yl group, a 4-phenylbenzothiophen-5-yl group, a 6-phenylbenzothiophen-5-yl group, a 7-phenylbenzothiophen-5-yl group, a 2-phenylbenzothiophen-6-yl group, a 3-phenylbenzothiophen-6-yl group, a 4-phenylbenzothiophen-6-yl group, a 5-phenylbenzothiophen-6-yl group, a 7-phenylbenzothiophen-6-yl group, a 2-phenylbenzothiophen-7-yl group, a 3-phenylbenzothiophen-7-yl group, a 4-phenylbenzothiophen-7-yl group, a 5-phenylbenzothiophen-7-yl group, and a 6-phenylbenzothiophen-7-yl group.

[0065] (20): 3-phenylbenzofuran-2-yl group, 4-phenylbenzofuran-2-yl group, 5-phenylbenzofuran-2-yl group, 6-phenylbenzofuran-2-yl group, 7-phenylbenzofuran-2-yl group, 2-phenylbenzofuran-3-yl group, 4-phenylbenzofuran-3-yl group, 5-phenylbenzofuran-3-yl group, 6-phenylbenzofuran-3-yl group, 7-phenylbenzofuran-3-yl group, 2-phenylbenzofuran-4-yl group, 3-phenylbenzofuran-4-yl group, 5-phenylbenzofuran-4-yl group, 6-phenylbenzofuran-4-yl group, 7-phenylbenzofuran-4-yl group and 6-phenylbenzofuran-7-yl groups.

[0066] (21): 2-phenyldibenzothiophene-1-yl group, 3-phenyldibenzothiophene-1-yl group, 4-phenyldibenzothiophene-1-yl group, 6-phenyldibenzothiophene-1-yl group, 7-phenyldibenzothiophene-1-yl group, 8-phenyldibenzothiophene-1-yl group, 9-phenyldibenzothiophene-1-yl group, 1-phenyldibenzothiophene-2-yl group, 3-phenyldibenzothiophene-2-yl group, 4-phenyldibenzothiophene-2 ​​... and 9-phenyldibenzothiophen-3-yl groups.

[0067] (22): 2-phenyldibenzofuran-1-yl group, 3-phenyldibenzofuran-1-yl group, 4-phenyldibenzofuran-1-yl group, 6-phenyldibenzofuran-1-yl group, 7-phenyldibenzofuran-1-yl group, 8-phenyldibenzofuran-1-yl group, 9-phenyldibenzofuran-1-yl group, 1-phenyldibenzofuran-2-yl group, 3-phenyldibenzofuran-2-yl group, 4-phenyldibenzofuran-2 ... Benzofuran-2-yl group, 7-phenyldibenzofuran-2-yl group, 8-phenyldibenzofuran-2-yl group, 9-phenyldibenzofuran-2-yl group, 1-phenyldibenzofuran-3-yl group, 2-phenyldibenzofuran-3-yl group, 4-phenyldibenzofuran-3-yl group, 6-phenyldibenzofuran-3-yl group, 7-phenyldibenzofuran-3-yl group, 8-phenyldibenzofuran-3-yl group, and 9-phenyldibenzofuran-3-yl group.

[0068] (23): 3-(2-pyridyl)thiophen-2-yl group, 4-(2-pyridyl)thiophen-2-yl group, 5-(2-pyridyl)thiophen-2-yl group, 2-(2-pyridyl)thiophen-3-yl group, 4-(2-pyridyl)thiophen-3-yl group, 5-(2-pyridyl)thiophen-3-yl group, 3-(2-pyridyl)furan-2-yl group, 4-(2-pyridyl)furan-2-yl group, 5-(2-pyridyl)furan-2-yl group, 2-(2-pyridyl)furan-3-yl group, 4-(2-pyridyl)furan-3-yl group, 5-(2-pyridyl)furan-3-yl group.

[0069] (24): 3-(2-pyridyl)benzothiophen-2-yl group, 4-(2-pyridyl)benzothiophen-2-yl group, 5-(2-pyridyl)benzothiophen-2-yl group, 6-(2-pyridyl)benzothiophen-2-yl group, 7-(2-pyridyl)benzothiophen-2-yl group, 2-(2-pyridyl)benzothiophen-3-yl group, 4-(2-pyridyl)benzothiophen-3-yl group, 5-(2-pyridyl)benzothiophen-2-yl group, (2-pyridyl)benzothiophen-3-yl group, 6-(2-pyridyl)benzothiophen-3-yl group, 7-(2-pyridyl)benzothiophen-3-yl group, 2-(2-pyridyl)benzothiophen-4-yl group, 3-(2-pyridyl)benzothiophen-4-yl group, 5-(2-pyridyl)benzothiophen-4-yl group, 6-(2-pyridyl)benzothiophen-4-yl group, 7-(2-pyridyl)benzothiophen-4-yl group 2-(2-pyridyl)benzothiophen-5-yl group, 3-(2-pyridyl)benzothiophen-5-yl group, 4-(2-pyridyl)benzothiophen-5-yl group, 6-(2-pyridyl)benzothiophen-5-yl group, 7-(2-pyridyl)benzothiophen-5-yl group, 2-(2-pyridyl)benzothiophen-6-yl group, 3-(2-pyridyl)benzothiophen-6-yl group, 4-(2-pyridyl)benzothiophen-5-yl group, benzothiophen-6-yl group, 5-(2-pyridyl)benzothiophen-6-yl group, 7-(2-pyridyl)benzothiophen-6-yl group, 2-(2-pyridyl)benzothiophen-7-yl group, 3-(2-pyridyl)benzothiophen-7-yl group, 4-(2-pyridyl)benzothiophen-7-yl group, 5-(2-pyridyl)benzothiophen-7-yl group, and 6-(2-pyridyl)benzothiophen-7-yl group.

[0070] (25): 3-(2-pyridyl)benzofuran-2-yl group, 4-(2-pyridyl)benzofuran-2-yl group, 5-(2-pyridyl)benzofuran-2-yl group, 6-(2-pyridyl)benzofuran-2-yl group, 7-(2-pyridyl)benzofuran-2-yl group, 2-(2-pyridyl)benzofuran-3-yl group, 4-(2-pyridyl)benzofuran-3-yl group, 5-(2-pyridyl)benzofuran-3-yl group, 6-(2-pyridyl)benzofuran-3-yl group, 7-(2-pyridyl)benzofuran-3-yl group, 2-(2-pyridyl)benzofuran-4-yl group, 3-(2-pyridyl)benzofuran-4-yl group, 5-(2-pyridyl)benzofuran-4-yl group, 6-(2-pyridyl)benzofuran-4-yl group, 7-(2-pyridyl)benzofuran-4-yl group benzofuran-5-yl group, 2-(2-pyridyl)benzofuran-5-yl group, 3-(2-pyridyl)benzofuran-5-yl group, 4-(2-pyridyl)benzofuran-5-yl group, 6-(2-pyridyl)benzofuran-5-yl group, 7-(2-pyridyl)benzofuran-5-yl group, 2-(2-pyridyl)benzofuran-6-yl group, 3-(2-pyridyl)benzofuran-6-yl group, 4-(2-pyridyl)benzofuran-6-yl group, 5-(2-pyridyl)benzofuran-6-yl group, 7-(2-pyridyl)benzofuran-6-yl group, 2-(2-pyridyl)benzofuran-7-yl group, 3-(2-pyridyl)benzofuran-7-yl group, 4-(2-pyridyl)benzofuran-7-yl group, 5-(2-pyridyl)benzofuran-7-yl group, and 6-(2-pyridyl)benzofuran-7-yl group.

[0071] (26): 2-(2-pyridyl)dibenzothiophen-1-yl group, 3-(2-pyridyl)dibenzothiophen-1-yl group, 4-(2-pyridyl)dibenzothiophen-1-yl group, 6-(2-pyridyl)dibenzothiophen-1-yl group, 7-(2-pyridyl)dibenzothiophen-1-yl group, 8-(2-pyridyl)dibenzothiophen-1-yl group, 9-(2-pyridyl)dibenzothiophen-1-yl group, 1-(2-pyridyl)dibenzothiophen-2-yl group, 3-(2-pyridyl)dibenzothiophen-2-yl group, 4-(2-pyridyl)dibenzothiophen-2-yl group, 6-(2-pyridyl)dibenzothiophen-1-yl group Dibenzothiophen-2-yl group, 7-(2-pyridyl)dibenzothiophen-2-yl group, 8-(2-pyridyl)dibenzothiophen-2-yl group, 9-(2-pyridyl)dibenzothiophen-2-yl group, 1-(2-pyridyl)dibenzothiophen-3-yl group, 2-(2-pyridyl)dibenzothiophen-3-yl group, 4-(2-pyridyl)dibenzothiophen-3-yl group, 6-(2-pyridyl)dibenzothiophen-3-yl group, 7-(2-pyridyl)dibenzothiophen-3-yl group, 8-(2-pyridyl)dibenzothiophen-3-yl group, 9-(2-pyridyl)dibenzothiophen-3-yl group.

[0072] (27): 2-(2-pyridyl)dibenzofuran-1-yl group, 3-(2-pyridyl)dibenzofuran-1-yl group, 4-(2-pyridyl)dibenzofuran-1-yl group, 6-(2-pyridyl)dibenzofuran-1-yl group, 7-(2-pyridyl)dibenzofuran-1-yl group, 8-(2-pyridyl)dibenzofuran-1-yl group, 9-(2-pyridyl)dibenzofuran-1-yl group, 1-(2-pyridyl)dibenzofuran-2-yl group, 3-(2-pyridyl)dibenzofuran-2-yl group, 4-(2-pyridyl)dibenzofuran-2 ... ) dibenzofuran-2-yl group, 7-(2-pyridyl)dibenzofuran-2-yl group, 8-(2-pyridyl)dibenzofuran-2-yl group, 9-(2-pyridyl)dibenzofuran-2-yl group, 1-(2-pyridyl)dibenzofuran-3-yl group, 2-(2-pyridyl)dibenzofuran-3-yl group, 4-(2-pyridyl)dibenzofuran-3-yl group, 6-(2-pyridyl)dibenzofuran-3-yl group, 7-(2-pyridyl)dibenzofuran-3-yl group, 8-(2-pyridyl)dibenzofuran-3-yl group, 9-(2-pyridyl)dibenzofuran-3-yl group.

[0073] (28): 3-(3-pyridyl)thiophen-2-yl group, 4-(3-pyridyl)thiophen-2-yl group, 5-(3-pyridyl)thiophen-2-yl group, 2-(3-pyridyl)thiophen-3-yl group, 4-(3-pyridyl)thiophen-3-yl group, 5-(3-pyridyl)thiophen-3-yl group.

[0074] (29): 3-(3-pyridyl)furan-2-yl group, 4-(3-pyridyl)furan-2-yl group, 5-(3-pyridyl)furan-2-yl group, 2-(3-pyridyl)furan-3-yl group, 4-(3-pyridyl)furan-3-yl group, 5-(3-pyridyl)furan-3-yl group.

[0075] (30): 3-(3-pyridyl)benzothiophen-2-yl group, 4-(3-pyridyl)benzothiophen-2-yl group, 5-(3-pyridyl)benzothiophen-2-yl group, 6-(3-pyridyl)benzothiophen-2-yl group, 7-(3-pyridyl)benzothiophen-2-yl group, 2-(3-pyridyl)benzothiophen-3-yl group, 4-(3-pyridyl)benzothiophen-3-yl group, 5-(3-pyridyl)benzothiophen-2-yl group, (3-pyridyl)benzothiophen-3-yl group, 6-(3-pyridyl)benzothiophen-3-yl group, 7-(3-pyridyl)benzothiophen-3-yl group, 2-(3-pyridyl)benzothiophen-4-yl group, 3-(3-pyridyl)benzothiophen-4-yl group, 5-(3-pyridyl)benzothiophen-4-yl group, 6-(3-pyridyl)benzothiophen-4-yl group, 7-(3-pyridyl)benzothiophen-4-yl group 2-(3-pyridyl)benzothiophen-5-yl group, 3-(3-pyridyl)benzothiophen-5-yl group, 4-(3-pyridyl)benzothiophen-5-yl group, 6-(3-pyridyl)benzothiophen-5-yl group, 7-(3-pyridyl)benzothiophen-5-yl group, 2-(3-pyridyl)benzothiophen-6-yl group, 3-(3-pyridyl)benzothiophen-6 ... benzothiophen-6-yl group, 5-(3-pyridyl)benzothiophen-6-yl group, 7-(3-pyridyl)benzothiophen-6-yl group, 2-(3-pyridyl)benzothiophen-7-yl group, 3-(3-pyridyl)benzothiophen-7-yl group, 4-(3-pyridyl)benzothiophen-7-yl group, 5-(3-pyridyl)benzothiophen-7-yl group, 6-(3-pyridyl)benzothiophen-7-yl group.

[0076] (31): 3-(3-pyridyl)benzofuran-2-yl group, 4-(3-pyridyl)benzofuran-2-yl group, 5-(3-pyridyl)benzofuran-2-yl group, 6-(3-pyridyl)benzofuran-2-yl group, 7-(3-pyridyl)benzofuran-2-yl group, 2-(3-pyridyl)benzofuran-3-yl group, 4-(3-pyridyl)benzofuran-3-yl group, 5-(3-pyridyl)benzofuran-3-yl group, 6-(3-pyridyl)benzofuran-3-yl group, 7-(3-pyridyl)benzofuran-3-yl group, 2-(3-pyridyl)benzofuran-4-yl group, 3-(3-pyridyl)benzofuran-4-yl group, 5-(3-pyridyl)benzofuran-4-yl group, 6-(3-pyridyl)benzofuran-4-yl group, 7-(3-pyridyl)benzofuran-4-yl group benzofuran-5-yl group, 2-(3-pyridyl)benzofuran-5-yl group, 3-(3-pyridyl)benzofuran-5-yl group, 4-(3-pyridyl)benzofuran-5-yl group, 6-(3-pyridyl)benzofuran-5-yl group, 7-(3-pyridyl)benzofuran-5-yl group, 2-(3-pyridyl)benzofuran-6-yl group, 3-(3-pyridyl)benzofuran-6-yl group, 4-(3-pyridyl)benzofuran-6-yl group, 5-(3-pyridyl)benzofuran-6-yl group, 7-(3-pyridyl)benzofuran-6-yl group, 2-(3-pyridyl)benzofuran-7-yl group, 3-(3-pyridyl)benzofuran-7-yl group, 4-(3-pyridyl)benzofuran-7-yl group, 5-(3-pyridyl)benzofuran-7-yl group, and 6-(3-pyridyl)benzofuran-7-yl group.

[0077] (32): 2-(3-pyridyl)dibenzothiophen-1-yl group, 3-(3-pyridyl)dibenzothiophen-1-yl group, 4-(3-pyridyl)dibenzothiophen-1-yl group, 6-(3-pyridyl)dibenzothiophen-1-yl group, 7-(3-pyridyl)dibenzothiophen-1-yl group, 8-(3-pyridyl)dibenzothiophen-1-yl group, 9-(3-pyridyl)dibenzothiophen-1-yl group, 1-(3-pyridyl)dibenzothiophen-2-yl group, 3-(3-pyridyl)dibenzothiophen-2-yl group, 4-(3-pyridyl)dibenzothiophen-2-yl group, 6-(3-pyridyl) Dibenzothiophen-2-yl group, 7-(3-pyridyl)dibenzothiophen-2-yl group, 8-(3-pyridyl)dibenzothiophen-2-yl group, 9-(3-pyridyl)dibenzothiophen-2-yl group, 1-(3-pyridyl)dibenzothiophen-3-yl group, 2-(3-pyridyl)dibenzothiophen-3-yl group, 4-(3-pyridyl)dibenzothiophen-3-yl group, 6-(3-pyridyl)dibenzothiophen-3-yl group, 7-(3-pyridyl)dibenzothiophen-3-yl group, 8-(3-pyridyl)dibenzothiophen-3-yl group, 9-(3-pyridyl)dibenzothiophen-3-yl group.

[0078] (33): 2-(3-pyridyl)dibenzofuran-1-yl group, 3-(3-pyridyl)dibenzofuran-1-yl group, 4-(3-pyridyl)dibenzofuran-1-yl group, 6-(3-pyridyl)dibenzofuran-1-yl group, 7-(3-pyridyl)dibenzofuran-1-yl group, 8-(3-pyridyl)dibenzofuran-1-yl group, 9-(3-pyridyl)dibenzofuran-1-yl group, 1-(3-pyridyl)dibenzofuran-2-yl group, 3-(3-pyridyl)dibenzofuran-2-yl group, 4-(3-pyridyl)dibenzofuran-2-yl group, 6-(3-pyridyl)dibenzofuran-1-yl group, ) dibenzofuran-2-yl group, 7-(3-pyridyl)dibenzofuran-2-yl group, 8-(3-pyridyl)dibenzofuran-2-yl group, 9-(3-pyridyl)dibenzofuran-2-yl group, 1-(3-pyridyl)dibenzofuran-3-yl group, 2-(3-pyridyl)dibenzofuran-3-yl group, 4-(3-pyridyl)dibenzofuran-3-yl group, 6-(3-pyridyl)dibenzofuran-3-yl group, 7-(3-pyridyl)dibenzofuran-3-yl group, 8-(3-pyridyl)dibenzofuran-3-yl group, 9-(3-pyridyl)dibenzofuran-3-yl group.

[0079] (34): 3-(4-pyridyl)thiophen-2-yl group, 4-(4-pyridyl)thiophen-2-yl group, 5-(4-pyridyl)thiophen-2-yl group, 2-(4-pyridyl)thiophen-3-yl group, 4-(4-pyridyl)thiophen-3-yl group, and 5-(4-pyridyl)thiophen-3-yl group.

[0080] (35): 3-(4-pyridyl)furan-2-yl group, 4-(4-pyridyl)furan-2-yl group, 5-(4-pyridyl)furan-2-yl group, 2-(4-pyridyl)furan-3-yl group, 4-(4-pyridyl)furan-3-yl group, and 5-(4-pyridyl)furan-3-yl group.

[0081] (36): 3-(4-pyridyl)benzothiophen-2-yl group, 4-(4-pyridyl)benzothiophen-2-yl group, 5-(4-pyridyl)benzothiophen-2-yl group, 6-(4-pyridyl)benzothiophen-2-yl group, 7-(4-pyridyl)benzothiophen-2-yl group, 2-(4-pyridyl)benzothiophen-3-yl group, 4-(4-pyridyl)benzothiophen-3-yl group, 5-(4-pyridyl)benzothiophen-2-yl group, (4-pyridyl)benzothiophen-3-yl group, 6-(4-pyridyl)benzothiophen-3-yl group, 7-(4-pyridyl)benzothiophen-3-yl group, 2-(4-pyridyl)benzothiophen-4-yl group, 3-(4-pyridyl)benzothiophen-4-yl group, 5-(4-pyridyl)benzothiophen-4-yl group, 6-(4-pyridyl)benzothiophen-4-yl group, 7-(4-pyridyl)benzothiophen-4-yl group 2-(4-pyridyl)benzothiophen-5-yl group, 3-(4-pyridyl)benzothiophen-5-yl group, 4-(4-pyridyl)benzothiophen-5-yl group, 6-(4-pyridyl)benzothiophen-5-yl group, 7-(4-pyridyl)benzothiophen-5-yl group, 2-(4-pyridyl)benzothiophen-6-yl group, 3-(4-pyridyl)benzothiophen-6-yl group, 4-(4-pyridyl)benzothiophen-5-yl group, benzothiophen-6-yl group, 5-(4-pyridyl)benzothiophen-6-yl group, 7-(4-pyridyl)benzothiophen-6-yl group, 2-(4-pyridyl)benzothiophen-7-yl group, 3-(4-pyridyl)benzothiophen-7-yl group, 4-(4-pyridyl)benzothiophen-7-yl group, 5-(4-pyridyl)benzothiophen-7-yl group, and 6-(4-pyridyl)benzothiophen-7-yl group.

[0082] (37): 3-(4-pyridyl)benzofuran-2-yl group, 4-(4-pyridyl)benzofuran-2-yl group, 5-(4-pyridyl)benzofuran-2-yl group, 6-(4-pyridyl)benzofuran-2-yl group, 7-(4-pyridyl)benzofuran-2-yl group, 2-(4-pyridyl)benzofuran-3-yl group, 4-(4-pyridyl)benzofuran-3-yl group, 5-(4-pyridyl)benzofuran-3-yl group, 6-(4-pyridyl)benzofuran-3-yl group, 7-(4-pyridyl)benzofuran-3-yl group, 2-(4-pyridyl)benzofuran-4-yl group, 3-(4-pyridyl)benzofuran-4-yl group, 5-(4-pyridyl)benzofuran-4-yl group, 6-(4-pyridyl)benzofuran-4-yl group, 7-(4-pyridyl)benzofuran-4-yl group benzofuran-5-yl group, 2-(4-pyridyl)benzofuran-5-yl group, 3-(4-pyridyl)benzofuran-5-yl group, 4-(4-pyridyl)benzofuran-5-yl group, 6-(4-pyridyl)benzofuran-5-yl group, 7-(4-pyridyl)benzofuran-5-yl group, 2-(4-pyridyl)benzofuran-6-yl group, 3-(4-pyridyl)benzofuran-6-yl group, 4-(4-pyridyl)benzofuran-6-yl group, 5-(4-pyridyl)benzofuran-6-yl group, 7-(4-pyridyl)benzofuran-6-yl group, 2-(4-pyridyl)benzofuran-7-yl group, 3-(4-pyridyl)benzofuran-7-yl group, 4-(4-pyridyl)benzofuran-7-yl group, 5-(4-pyridyl)benzofuran-7-yl group, and 6-(4-pyridyl)benzofuran-7-yl group.

[0083] (38): 2-(4-pyridyl)dibenzothiophen-1-yl group, 3-(4-pyridyl)dibenzothiophen-1-yl group, 4-(4-pyridyl)dibenzothiophen-1-yl group, 6-(4-pyridyl)dibenzothiophen-1-yl group, 7-(4-pyridyl)dibenzothiophen-1-yl group, 8-(4-pyridyl)dibenzothiophen-1-yl group, 9-(4-pyridyl)dibenzothiophen-1-yl group, 1-(4-pyridyl)dibenzothiophen-2-yl group, 3-(4-pyridyl)dibenzothiophen-2-yl group, 4-(4-pyridyl)dibenzothiophen-2-yl group, 6-(4-pyridyl)dibenzothiophen-1-yl group Dibenzothiophen-2-yl group, 7-(4-pyridyl)dibenzothiophen-2-yl group, 8-(4-pyridyl)dibenzothiophen-2-yl group, 9-(4-pyridyl)dibenzothiophen-2-yl group, 1-(4-pyridyl)dibenzothiophen-3-yl group, 2-(4-pyridyl)dibenzothiophen-3-yl group, 4-(4-pyridyl)dibenzothiophen-3-yl group, 6-(4-pyridyl)dibenzothiophen-3-yl group, 7-(4-pyridyl)dibenzothiophen-3-yl group, 8-(4-pyridyl)dibenzothiophen-3-yl group, 9-(4-pyridyl)dibenzothiophen-3-yl group.

[0084] (39): 2-(4-pyridyl)dibenzofuran-1-yl group, 3-(4-pyridyl)dibenzofuran-1-yl group, 4-(4-pyridyl)dibenzofuran-1-yl group, 6-(4-pyridyl)dibenzofuran-1-yl group, 7-(4-pyridyl)dibenzofuran-1-yl group, 8-(4-pyridyl)dibenzofuran-1-yl group, 9-(4-pyridyl)dibenzofuran-1-yl group, 1-(4-pyridyl)dibenzofuran-2-yl group, 3-(4-pyridyl)dibenzofuran-2-yl group, 4-(4-pyridyl)dibenzofuran-2 ...2-yl group, ) dibenzofuran-2-yl group, 7-(4-pyridyl)dibenzofuran-2-yl group, 8-(4-pyridyl)dibenzofuran-2-yl group, 9-(4-pyridyl)dibenzofuran-2-yl group, 1-(4-pyridyl)dibenzofuran-3-yl group, 2-(4-pyridyl)dibenzofuran-3-yl group, 4-(4-pyridyl)dibenzofuran-3-yl group, 6-(4-pyridyl)dibenzofuran-3-yl group, 7-(4-pyridyl)dibenzofuran-3-yl group, 8-(4-pyridyl)dibenzofuran-3-yl group, 9-(4-pyridyl)dibenzofuran-3-yl group.

[0085] (40): 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9,9-dimethylfluoren-1-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, 9,9-diphenylfluoren-1-yl group, 9,9-diphenylfluoren-2-yl group, 9,9-diphenylfluoren-3-yl group, and 9,9-diphenylfluoren-4-yl group.

[0086] (41): 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(1-anthryl)phenyl group, 3-(1-anthryl)phenyl group , 4-(1-anthryl)phenyl group, 2-(2-anthryl)phenyl group, 3-(2-anthryl)phenyl group, 4-(2-anthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9-anthryl)phenyl group, 2-(1-pyrenyl)phenyl group, 3-(1-pyrenyl)phenyl group, 4-(1-pyrenyl)phenyl group, 2-(2-pyrenyl)phenyl group, 3-(2-pyrenyl)phenyl group (2-pyrenyl)phenyl group, 4-(2-pyrenyl)phenyl group, 2-(2-fluoranthenyl)phenyl group, 3-(2-fluoranthenyl)phenyl group, 4-(2-fluoranthenyl)phenyl group, 2-(3-fluoranthenyl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 2-(7-fluoranthenyl)phenyl group, 3-(7-fluoranthenyl)phenyl group, 4-(7-fluoranthenyl)phenyl group, (fluoranthenyl)phenyl group, 2-(8-fluoranthenyl)phenyl group, 3-(8-fluoranthenyl)phenyl group, 4-(8-fluoranthenyl)phenyl group, 2-(1-triphenylenyl)phenyl group, 3-(1-triphenylenyl)phenyl group, 4-(1-triphenylenyl)phenyl group, 2-(2-triphenylenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group.

[0087] (42): 2-(2-quinolyl)phenyl group, 3-(2-quinolyl)phenyl group, 4-(2-quinolyl)phenyl group, 2-(3-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 2-(4-quinolyl)phenyl group, 3-(4-quinolyl)phenyl group, 4-(4-quinolyl)phenyl group, 2-(5-quinolyl)phenyl group, 3-(5-quinolyl)phenyl group group, 4-(5-quinolyl)phenyl group, 2-(6-quinolyl)phenyl group, 3-(6-quinolyl)phenyl group, 4-(6-quinolyl)phenyl group, 2-(7-quinolyl)phenyl group, 3-(7-quinolyl)phenyl group, 4-(7-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(1-isoquinolyl)phenyl group, 3-(1-isoquinolyl)phenyl group, 4-(1-isoquinolyl)phenyl group, 2-(3-isoquinolyl)phenyl group, 3-(3-isoquinolyl)phenyl group, 4-(3-isoquinolyl)phenyl group, 2-(4-isoquinolyl)phenyl group, 3-(4-isoquinolyl)phenyl group, 4-(4-isoquinolyl)phenyl group, 2-(5-isoquinolyl)phenyl group, 3-(5-isoquinolyl)phenyl group, 4-(5-isoquinolyl)phenyl group, 2-(6-isoquinolyl)phenyl group, 3-(6-isoquinolyl)phenyl group, 4-(6-isoquinolyl)phenyl group, 2-(7-isoquinolyl)phenyl group, 3-(7-isoquinolyl)phenyl group, 4-(7-isoquinolyl)phenyl group, 2-(8-isoquinolyl)phenyl group, 3-(8-isoquinolyl)phenyl group, and 4-(8-isoquinolyl)phenyl group.

[0088] (43): 2-(2-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 4-(2-benzothienyl)phenyl group, 2-(3-benzothienyl)phenyl group, 3-(3-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 2-(4-benzothienyl)phenyl group, 3-(4-benzothienyl)phenyl group, 4-(4-benzothienyl)phenyl group, 2-(5-benzothienyl)phenyl group, 3-(5-benzothienyl)phenyl group, 4-(5-benzothienyl)phenyl group, 2-(6-benzothienyl)phenyl group, 3-(6-benzothienyl)phenyl group, 4-(6-benzothienyl)phenyl group, 2-(7-benzothienyl)phenyl group, 3-(7-benzothienyl)phenyl group, 4-(7-benzothienyl)phenyl group, zothienyl)phenyl group, 2-(2-benzofuryl)phenyl group, 3-(2-benzofuryl)phenyl group, 4-(2-benzofuryl)phenyl group, 2-(3-benzofuryl)phenyl group, 3-(3-benzofuryl)phenyl group, 4-(3-benzofuryl)phenyl group, 2-(4-benzofuryl)phenyl group, 3-(4-benzofuryl)phenyl group, 4-(4-benzofuryl)phenyl group, 2-(5-benzofuryl)phenyl group, 3-(5-benzofuryl)phenyl group, 4-(5-benzofuryl)phenyl group, 2-(6-benzofuryl)phenyl group, 3-(6-benzofuryl)phenyl group, 4-(6-benzofuryl)phenyl group, 2-(7-benzofuryl)phenyl group, 3-(7-benzofuryl)phenyl group, 4-(7-benzofuryl)phenyl group.

[0089] (44): 2-(1-dibenzothienyl)phenyl group, 3-(1-dibenzothienyl)phenyl group, 4-(1-dibenzothienyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 2-(3-dibenzothienyl)phenyl group, 3-(3-dibenzothienyl)phenyl group, 4-(3-dibenzothienyl)phenyl group, 2-(4-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, phenyl group, 2-(1-dibenzofuryl)phenyl group, 3-(1-dibenzofuryl)phenyl group, 4-(1-dibenzofuryl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(3-dibenzofuryl)phenyl group, 3-(3-dibenzofuryl)phenyl group, 4-(3-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, and 4-(4-dibenzofuryl)phenyl group.

[0090] Among these substituents, the following are particularly preferred because of their excellent electron transporting material properties: phenyl group, p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 2-(2-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9-anthryl)phenyl group, 2-(3-fluoranthenyl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 2-(2-triphenylenyl) Phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 2-(3-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group , 2-(4-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 4-quinolyl group, 8-quinolyl group, 3-isoquinolyl group,A 2-benzothienyl group, a 2-benzofuryl group, a 9-anthryl group, a 9-phenanthryl group, a 2-dibenzothienyl group, a 2-dibenzofuryl group, a 4-dibenzothienyl group, a 4-dibenzofuryl group, a 3-fluoranthenyl group, a 1-pyrenyl group, a 2-triphenylenyl group, etc. are preferred. Among these substituents, from the viewpoint of excellent electron transport material properties, a phenyl group, a p-tolyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3-(2-pyridyl)phenyl group, a 4-(2-pyridyl)phenyl group, a 3-(3-pyridyl)phenyl group, a 4-(3-pyridyl)phenyl group, a 3-(4-pyridyl)phenyl group, a 4-(4-pyridyl)phenyl group, a 2-(1-naphthyl)phenyl group, a 3-(1-naphthyl)phenyl group are preferred. , 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 3-(3-quinol aryl)phenyl group, 4-(3-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2 More preferred are 4-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 1-naphthyl group, 2-naphthyl group, 3-quinolyl group, 8-quinolyl group, 2-benzothienyl group, 2-benzofuryl group, 9-anthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, and 4-dibenzofuryl group.

[0091] Ar13 The total number of ring-constituting carbon atoms of the group represented by 14 The total number of ring-constituting carbon atoms of the group represented by the formula (I) is 4 to 25. 13 The total number of ring carbon atoms of the group represented by 14 The total number of ring-constituting carbon atoms is preferably 4 to 20 in each case. In addition, Ar 13 , Ar 14 When Ar has a substituent, the number of carbon atoms of the substituent is 13 , Ar 14 Therefore, for example, Ar 13 A diphenylfluorene group (having 25 ring carbon atoms) represented by the formula: 13 When the group represented by the formula (I) has a phenyl group, the diphenylfluorene group having a phenyl group is 13 ) totaling 31 ring carbon atoms.

[0092] Ar 13 The total number of ring carbon atoms of Ar 14 The total number of ring-constituting carbon atoms of and the sum of are preferably 8 to 32.

[0093] [Z 11 , Z 12 About Z 11 and Z 12 one of them represents a nitrogen atom and the other represents CH. [L 11 About L 11 represents a phenylene group or a single bond. 11 is preferably a single bond. [n 11 About n 11 represents 1 or 2. In terms of ease of synthesis, n 11 is preferably 1.

[0094] [Ar 21, Ar 22 About Ar 21 , Ar 22 each independently represents a phenyl group, a biphenyl group, or a naphthyl group. Ar 21 , Ar 22 Each group represented by the following formula (I) may be independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group.

[0095] -Ar 21 , -Ar 22 Preferred examples of the group represented by the formula include the groups (A) to (C) shown below.

[0096] (A): Phenyl group, p-methylphenyl group, m-methylphenyl group, o-methylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, and mesityl group. (B): biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl-2-yl group, 4'-methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group. (C): 1-naphthyl group, 2-naphthyl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalen-7-yl group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalen-5-yl group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-8-yl group.

[0097] Among these substituents, a phenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, a 2-naphthyl group, and the like are preferred in terms of excellent electron transporting material properties.

[0098] Ar 21 and Ar 22 may be the same as or different from each other. Ar 21 and Ar 22 are preferably identical to each other since this facilitates manufacture. Ar 21 and Ar 22 When the molecular weights are different from each other, the compound has high solubility in organic solvents, which is preferable.

[0099] [Ar 23 About Ar 23 is an optionally linked monocyclic ring, an optionally linked condensed ring, or a structure in which these are linked together, (i) an aromatic hydrocarbon group having 6 to 18 carbon atoms; (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings; (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S; (iv) a group formed by a combination of any two or more selected from the above (i) to (iii); Represents. -Ar 23 Each of the groups (i) to (iv) represented by the following formula may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a phenyl group.

[0100] Ar 23 The total number of ring-constituting carbon atoms of the group represented by the following formula is 4 to 25. In addition, Ar 23 When Ar has a substituent, the number of carbon atoms of the substituent is 23 Therefore, for example, Ar23 is a diphenylfluorene group (having 25 carbon atoms in the ring), and Ar 23 When the group represented by the formula (I) has a phenyl group, the diphenylfluorene group having a phenyl group is 23 ) totaling 31 ring carbon atoms.

[0101] Examples of the aromatic hydrocarbon group (i) include a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, an acenaphthyl group, etc. As described above, these substituents (aromatic hydrocarbon groups) may be substituted with a fluorine atom, a methyl group, or a phenyl group.

[0102] Examples of the heteroaromatic group (ii) include a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, a dibenzofuryl group, etc. As described above, these substituents (aromatic hydrocarbon groups) may be substituted with a fluorine atom, a methyl group, or a phenyl group.

[0103] When the cyclic azine compound (1) is used as a part of a component of an organic electroluminescent device (OLED; organic light emitting diode), it is possible to obtain effects such as high luminous efficiency and low voltage. In particular, when the cyclic azine compound (1) is used as an electron transport layer, these effects are more pronounced.

[0104] -Ar 23 Preferred specific examples of the group represented by the formula include the groups (1) to (22) shown below.

[0105] (1): Phenyl group, p-methylphenyl group, m-methylphenyl group, o-methylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group

[0106] (2): biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl-2-yl group, 4'-methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group

[0107] (3): 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalen-4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalen-1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2 -Phenylnaphthalen-7-yl group, 2-phenylnaphthalen-8-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalen-7-yl group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalen-5-yl group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-8-yl group

[0108] (4): 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-phenylphenanthrene-2-yl group, 1-phenylphenanthrene-3-yl group, 1-phenylphenanthrene-4-yl group, 1-phenylphenanthrene-5-yl group, 1-phenylphenanthrene-6-yl group, 1-phenylphenanthrene-7-yl group, 1-phenylphenanthrene-8-yl group, 1-phenylphenanthrene-9-yl group, 1-phenylphenanthrene-10-yl group, 2-phenylphenanthrene group, anthren-1-yl group, 2-phenylphenanthrene-3-yl group, 2-phenylphenanthrene-4-yl group, 2-phenylphenanthrene-5-yl group, 2-phenylphenanthrene-6-yl group, 2-phenylphenanthrene-7-yl group, 2-phenylphenanthrene-8-yl group, 2-phenylphenanthrene-9-yl group, 2-phenylphenanthrene-10-yl group, 3-phenylphenanthrene-1-yl group, 3-phenylphenanthrene-2-yl group, 3-phenylphenanthrene-4-yl group, 3-phenylphenanthrene-5 -yl group, 3-phenylphenanthren-6-yl group, 3-phenylphenanthren-7-yl group, 3-phenylphenanthren-8-yl group, 3-phenylphenanthren-9-yl group, 3-phenylphenanthren-10-yl group, 4-phenylphenanthren-1-yl group, 4-phenylphenanthren-2-yl group, 4-phenylphenanthren-3-yl group, 4-phenylphenanthren-5-yl group, 4-phenylphenanthren-6-yl group, 4-phenylphenanthren-7-yl group, 4-phenylphenanthren-8-yl group, 4- phenylphenanthrene-9-yl group, 4-phenylphenanthrene-10-yl group, 1-methylphenanthrene-2-yl group, 1-methylphenanthrene-3-yl group, 1-methylphenanthrene-4-yl group, 1-methylphenanthrene-5-yl group, 1-methylphenanthrene-6-yl group, 1-methylphenanthrene-7-yl group, 1-methylphenanthrene-8-yl group, 1-methylphenanthrene-9-yl group, 1-methylphenanthrene-10-yl group, 2-methylphenanthrene-1-yl group, 2-methylphenanthrene-3-yl group,2-methylphenanthren-4-yl group, 2-methylphenanthren-5-yl group, 2-methylphenanthren-6-yl group, 2-methylphenanthren-7-yl group, 2-methylphenanthren-8-yl group, 2-methylphenanthren-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methylphenanthren-2-yl group, 3-methylphenanthren-4-yl group, 3-methylphenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren phenanthrene-7-yl group, 3-methylphenanthrene-8-yl group, 3-methylphenanthrene-9-yl group, 3-methylphenanthrene-10-yl group, 4-methylphenanthrene-1-yl group, 4-methylphenanthrene-2-yl group, 4-methylphenanthrene-3-yl group, 4-methylphenanthrene-5-yl group, 4-methylphenanthrene-6-yl group, 4-methylphenanthrene-7-yl group, 4-methylphenanthrene-8-yl group, 4-methylphenanthrene-9-yl group, 4-methylphenanthrene-10-yl group,

[0109] (5): 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenylanthracen-2-yl group, 1-phenylanthracen-3-yl group, 1-phenylanthracen-4-yl group, 1-phenylanthracen-5-yl group, 1-phenylanthracen-6-yl group, 1-phenylanthracen-7-yl group, 1-phenylanthracen-8-yl group, 1-phenylanthracen-9-yl group, 1-phenylanthracen-10-yl group, 2-phenylanthracen-1-yl group, 2-phenylanthracen -3-yl group, 2-phenylanthracen-4-yl group, 2-phenylanthracen-5-yl group, 2-phenylanthracen-6-yl group, 2-phenylanthracen-7-yl group, 2-phenylanthracen-8-yl group, 2-phenylanthracen-9-yl group, 2-phenylanthracen-10-yl group, 9-phenylanthracen-1-yl group, 9-phenylanthracen-2-yl group, 9-phenylanthracen-3-yl group, 9-phenylanthracen-4-yl group, 9-phenylanthracen-5-yl group

[0110] (6): 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-phenylpyren-2-yl group, 1-phenylpyren-3-yl group, 1-phenylpyren-4-yl group, 1-phenylpyren-5-yl group, 1-phenylpyren-6-yl group, 1-phenylpyren-7-yl group, 1-phenylpyren-8-yl group, 1-phenylpyren-9-yl group, 1-phenylpyren-10-yl group, 2-phenylpyren-1-yl group, 2-phenylpyren-3-yl group, 2-phenylpyren-4-yl group, yl group, 2-phenylpyren-5-yl group, 2-phenylpyren-6-yl group, 2-phenylpyren-7-yl group, 2-phenylpyren-8-yl group, 2-phenylpyren-9-yl group, 2-phenylpyren-10-yl group, 9-phenylpyren-1-yl group, 9-phenylpyren-2-yl group, 9-phenylpyren-3-yl group, 9-phenylpyren-4-yl group, 9-phenylpyren-5-yl group, 9-phenylpyren-6-yl group, 9-phenylpyren-7-yl group, 9 ... phenylpyren-8-yl group, 9-phenylpyren-10-yl group, 1-methylpyren-2-yl group, 1-methylpyren-3-yl group, 1-methylpyren-4-yl group, 1-methylpyren-5-yl group, 1-methylpyren-6-yl group, 1-methylpyren-7-yl group, 1-methylpyren-8-yl group, 1-methylpyren-9-yl group, 1-methylpyren-10-yl group, 2-methylpyren-1-yl group, 2-methylpyren-3-yl group, 2-methylpyren-4-yl group, 2-methylpyren -5-yl group, 2-methylpyren-6-yl group, 2-methylpyren-7-yl group, 2-methylpyren-8-yl group, 2-methylpyren-9-yl group, 2-methylpyren-10-yl group, 9-methylpyren-1-yl group, 9-methylpyren-2-yl group, 9-methylpyren-3-yl group, 9-methylpyren-4-yl group, 9-methylpyren-5-yl group, 9-methylpyren-6-yl group, 9-methylpyren-7-yl group, 9-methylpyren-8-yl group, 9-methylpyren-10-yl group

[0111] (7): triphenylene-1-yl group, triphenylene-2-yl group, acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group

[0112] (8): acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group

[0113] (9): 2-thienyl group, 3-thienyl group, 2-furyl group, 3-furyl group, benzothiophen-2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group, benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group, dibenzothiophen-1-yl group, dibenzothiophen-2-yl group, dibenzothiof dibenzofuran-3-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, 3-methylthiophen-2-yl group, 4-methylthiophen-2-yl group, 5-methylthiophen-2-yl group, 2-methylthiophen-3-yl group, 4-methylthiophen-3-yl group, 5-methylthiophen-3-yl group, 3-methylfuran-2-yl group, 4-methylfuran-2-yl group, 5-methylfuran-2-yl group, 2-methylfuran-3-yl group, 4-methylfuran-3-yl group, 5-methylfuran-3-yl group

[0114] (10): 3-methylbenzothiophene-2-yl group, 4-methylbenzothiophene-2-yl group, 5-methylbenzothiophene-2-yl group, 6-methylbenzothiophene-2-yl group, 7-methylbenzothiophene-2-yl group, 2-methylbenzothiophene-3-yl group, 4-methylbenzothiophene-3-yl group, 5-methylbenzothiophene-3-yl group, 6-methylbenzothiophene-3-yl group, 7-methylbenzothiophene-3-yl group, 2-methylbenzothiophene-4-yl group, 3-methylbenzothiophene-4-yl group, 5-methylbenzothiophene-4-yl group, 6-methylbenzothiophene-4-yl group, 7-methylbenzothiophene-4-yl group benzothiophene-5-yl group, 2-methylbenzothiophene-5-yl group, 3-methylbenzothiophene-5-yl group, 4-methylbenzothiophene-5-yl group, 6-methylbenzothiophene-5-yl group, 7-methylbenzothiophene-5-yl group, 2-methylbenzothiophene-6-yl group, 3-methylbenzothiophene-6-yl group, 4-methylbenzothiophene-6-yl group, 5-methylbenzothiophene-6-yl group, 7-methylbenzothiophene-6-yl group, 2-methylbenzothiophene-7-yl group, 3-methylbenzothiophene-7-yl group, 4-methylbenzothiophene-7-yl group, 5-methylbenzothiophene-7-yl group, 6-methylbenzothiophene-7-yl group

[0115] (11): 3-methylbenzofuran-2-yl group, 4-methylbenzofuran-2-yl group, 5-methylbenzofuran-2-yl group, 6-methylbenzofuran-2-yl group, 7-methylbenzofuran-2-yl group, 2-methylbenzofuran-3-yl group, 4-methylbenzofuran-3-yl group, 5-methylbenzofuran-3-yl group, 6-methylbenzofuran-3-yl group, 7-methylbenzofuran-3-yl group, 2-methylbenzofuran-4-yl group, 3-methylbenzofuran-4-yl group, 5-methylbenzofuran-4-yl group, 6-methylbenzofuran-4-yl group, 7-methylbenzofuran-4-yl group benzofuran-5-yl group, 2-methylbenzofuran-5-yl group, 3-methylbenzofuran-5-yl group, 4-methylbenzofuran-5-yl group, 6-methylbenzofuran-5-yl group, 7-methylbenzofuran-5-yl group, 2-methylbenzofuran-6-yl group, 3-methylbenzofuran-6-yl group, 4-methylbenzofuran-6-yl group, 5-methylbenzofuran-6-yl group, 7-methylbenzofuran-6-yl group, 2-methylbenzofuran-7-yl group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methylbenzofuran-7-yl group, 6-methylbenzofuran-7-yl group

[0116] (12): 2-methyldibenzothiophene-1-yl group, 3-methyldibenzothiophene-1-yl group, 4-methyldibenzothiophene-1-yl group, 6-methyldibenzothiophene-1-yl group, 7-methyldibenzothiophene-1-yl group, 8-methyldibenzothiophene-1-yl group, 9-methyldibenzothiophene-1-yl group, 1-methyldibenzothiophene-2-yl group, 3-methyldibenzothiophene-2-yl group, 4-methyldibenzothiophene-2 ​​... benzothiophen-2-yl group, 7-methyldibenzothiophen-2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyldibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group, 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothiophen-3-yl group, 9-methyldibenzothiophen-3-yl group

[0117] (13): 2-methyldibenzofuran-1-yl group, 3-methyldibenzofuran-1-yl group, 4-methyldibenzofuran-1-yl group, 6-methyldibenzofuran-1-yl group, 7-methyldibenzofuran-1-yl group, 8-methyldibenzofuran-1-yl group, 9-methyldibenzofuran-1-yl group, 1-methyldibenzofuran-2-yl group, 3-methyldibenzofuran-2-yl group, 4-methyldibenzofuran-2-yl group, 6-methyldibenzofuran Benzofuran-2-yl group, 7-methyldibenzofuran-2-yl group, 8-methyldibenzofuran-2-yl group, 9-methyldibenzofuran-2-yl group, 1-methyldibenzofuran-3-yl group, 2-methyldibenzofuran-3-yl group, 4-methyldibenzofuran-3-yl group, 6-methyldibenzofuran-3-yl group, 7-methyldibenzofuran-3-yl group, 8-methyldibenzofuran-3-yl group, 9-methyldibenzofuran-3-yl group

[0118] (14): 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenylthiophen-3-yl group, 4-phenylthiophen-3-yl group, 5-phenylthiophen-3-yl group

[0119] (15): 3-phenylfuran-2-yl group, 4-phenylfuran-2-yl group, 5-phenylfuran-2-yl group, 2-phenylfuran-3-yl group, 4-phenylfuran-3-yl group, 5-phenylfuran-3-yl group

[0120] (16): 3-phenylbenzothiophene-2-yl group, 4-phenylbenzothiophene-2-yl group, 5-phenylbenzothiophene-2-yl group, 6-phenylbenzothiophene-2-yl group, 7-phenylbenzothiophene-2-yl group, 2-phenylbenzothiophene-3-yl group, 4-phenylbenzothiophene-3-yl group, 5-phenylbenzothiophene-3-yl group, 6-phenylbenzothiophene-3-yl group, 7-phenylbenzothiophene-3-yl group, 2-phenylbenzothiophene-4-yl group, 3-phenylbenzothiophene-4-yl group, 5-phenylbenzothiophene-4-yl group, 6-phenylbenzothiophene-4-yl group, 7-phenylbenzothiophene-4-yl group phenylbenzothiophene-5-yl group, 2-phenylbenzothiophene-5-yl group, 3-phenylbenzothiophene-5-yl group, 4-phenylbenzothiophene-5-yl group, 6-phenylbenzothiophene-5-yl group, 7-phenylbenzothiophene-5-yl group, 2-phenylbenzothiophene-6-yl group, 3-phenylbenzothiophene-6-yl group, 4-phenylbenzothiophene-6-yl group, 5-phenylbenzothiophene-6-yl group, 7-phenylbenzothiophene-6-yl group, 2-phenylbenzothiophene-7-yl group, 3-phenylbenzothiophene-7-yl group, 4-phenylbenzothiophene-7-yl group, 5-phenylbenzothiophene-7-yl group, 6-phenylbenzothiophene-7-yl group

[0121] (17): 3-phenylbenzofuran-2-yl group, 4-phenylbenzofuran-2-yl group, 5-phenylbenzofuran-2-yl group, 6-phenylbenzofuran-2-yl group, 7-phenylbenzofuran-2-yl group, 2-phenylbenzofuran-3-yl group, 4-phenylbenzofuran-3-yl group, 5-phenylbenzofuran-3-yl group, 6-phenylbenzofuran-3-yl group, 7-phenylbenzofuran-3-yl group, 2-phenylbenzofuran-4-yl group, 3-phenylbenzofuran-4-yl group, 5-phenylbenzofuran-4-yl group, 6-phenylbenzofuran-4-yl group, 7-phenylbenzofuran-4-yl group benzofuran-5-yl group, 2-phenylbenzofuran-5-yl group, 3-phenylbenzofuran-5-yl group, 4-phenylbenzofuran-5-yl group, 6-phenylbenzofuran-5-yl group, 7-phenylbenzofuran-5-yl group, 2-phenylbenzofuran-6-yl group, 3-phenylbenzofuran-6-yl group, 4-phenylbenzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6-yl group, 2-phenylbenzofuran-7-yl group, 3-phenylbenzofuran-7-yl group, 4-phenylbenzofuran-7-yl group, 5-phenylbenzofuran-7-yl group, 6-phenylbenzofuran-7-yl group

[0122] (18): 2-phenyldibenzothiophene-1-yl group, 3-phenyldibenzothiophene-1-yl group, 4-phenyldibenzothiophene-1-yl group, 6-phenyldibenzothiophene-1-yl group, 7-phenyldibenzothiophene-1-yl group, 8-phenyldibenzothiophene-1-yl group, 9-phenyldibenzothiophene-1-yl group, 1-phenyldibenzothiophene-2-yl group, 3-phenyldibenzothiophene-2-yl group, 4-phenyldibenzothiophene-2 ​​... phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophen-2-yl group, 9-phenyldibenzothiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophen-3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl group, 7-phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophen-3-yl group, 9-phenyldibenzothiophen-3-yl group

[0123] (19): 2-phenyldibenzofuran-1-yl group, 3-phenyldibenzofuran-1-yl group, 4-phenyldibenzofuran-1-yl group, 6-phenyldibenzofuran-1-yl group, 7-phenyldibenzofuran-1-yl group, 8-phenyldibenzofuran-1-yl group, 9-phenyldibenzofuran-1-yl group, 1-phenyldibenzofuran-2-yl group, 3-phenyldibenzofuran-2-yl group, 4-phenyldibenzofuran-2 ... Benzofuran-2-yl group, 7-phenyldibenzofuran-2-yl group, 8-phenyldibenzofuran-2-yl group, 9-phenyldibenzofuran-2-yl group, 1-phenyldibenzofuran-3-yl group, 2-phenyldibenzofuran-3-yl group, 4-phenyldibenzofuran-3-yl group, 6-phenyldibenzofuran-3-yl group, 7-phenyldibenzofuran-3-yl group, 8-phenyldibenzofuran-3-yl group, 9-phenyldibenzofuran-3-yl group

[0124] (20): 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9,9-dimethylfluoren-1-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, 9,9-diphenylfluoren-1-yl group, 9,9-diphenylfluoren-2-yl group, 9,9-diphenylfluoren-3-yl group, 9,9-diphenylfluoren-4-yl group

[0125] (21): 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(1-anthryl)phenyl group, 3-(1-anthryl)phenyl group, 4-(1-anthryl) Phenyl group, 2-(2-anthryl)phenyl group, 3-(2-anthryl)phenyl group, 4-(2-anthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 4-(9-anthryl)phenyl group, 2-(1-pyrenyl)phenyl group, 3-(1-pyrenyl)phenyl group, 4-(1-pyrenyl)phenyl group, 2-(2-pyrenyl)phenyl group, 3-(2-pyrenyl)phenyl group, 4-(2-pyrenyl)phenyl group

[0126] (22): 2-(1-dibenzothienyl)phenyl group, 3-(1-dibenzothienyl)phenyl group, 4-(1-dibenzothienyl)phenyl group, 2-(2-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 2-(3-dibenzothienyl)phenyl group, 3-(3-dibenzothienyl)phenyl group, 4-(3-dibenzothienyl)phenyl group, 2-(4-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, nyl)phenyl group, 2-(1-dibenzofuryl)phenyl group, 3-(1-dibenzofuryl)phenyl group, 4-(1-dibenzofuryl)phenyl group, 2-(2-dibenzofuryl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzofuryl)phenyl group, 2-(3-dibenzofuryl)phenyl group, 3-(3-dibenzofuryl)phenyl group, 4-(3-dibenzofuryl)phenyl group, 2-(4-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group

[0127] Ar 23 is more preferably a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, an acenaphthyl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group, each of which may be substituted with a fluorine atom, a methyl group, or a phenyl group.

[0128] Ar 23 However, from the viewpoint of ease of synthesis, an unsubstituted phenyl group, biphenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, chrysenyl group, acenaphthyl group, benzothienyl group, dibenzofuryl group, or dibenzothienyl group is more preferred.

[0129] Ar 23However, in terms of excellent heat resistance, an unsubstituted fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, an acenaphthyl group, a benzothienyl group, a dibenzofuryl group, or a dibenzothienyl group is particularly preferred.

[0130] [S 1 About the Ring S 1 X in the ring 21 ~X 25 are each independently C-Ar 23 , CR, or a nitrogen atom. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. X 21 ~X 25 Only one of the C-Ar 23 It is. X 21 ~X 25 One or two of these are nitrogen atoms.

[0131] [n 21 , L 21 About n 21 represents the integers 0, 1, or 2. L 21 is a phenylene group or a single bond. X 21 ~X 25 Among them, X 21 and X 25 Either one of them is C-Ar 23 If so, L 21 is a single bond, n 21 is either 0 or 1. X 21 ~X 25 Of these, X 22 ~X 24 One of the following is C-Ar 23 If so, L 21 is a phenylene group or a single bond, n 21 is 0, 1, or 2.

[0132] S is easy to synthesize. 1 The ring is preferably a pyridylene group, a methylpyridylene group, a dimethylpyridylene group, or a pyrimidylene group.

[0133] Cyclic azine compounds represented by formula (22) Here, S 1 X in the ring 21 ~X 25 When one of the groups is a nitrogen atom, the cyclic azine compound (21) is a cyclic azine compound represented by the following formula (22):

[0134] [ka]

[0135] During the ceremony, Ar 21 ~Ar 23 , n 21 , L 21 R has the same meaning as in the cyclic azine compound (21); Y 21 ~Y 25 are each independently C-Ar 23 , CR, or a nitrogen atom; Y 21 ~Y 25 Of these, only one is a nitrogen atom; Y 21 ~Y 25 Only one of the C-Ar 23 is; Y 21 ~Y 25 Of these, Y 21 and Y 25 Either one of them is C-Ar 23 If so, L 21 is a single bond, n 21 is 0 or 1; Y 21 ~Y 25 Among them, Y 22 ~Y 24One of the following is C-Ar 23 If so, L 21 is a phenylene group or a single bond, n 21 is 0, 1, or 2.

[0136] Cyclic azine compounds represented by formula (23): Here, S 1 X in the ring 21 ~X 25 In the case where two of the groups are nitrogen atoms, the cyclic azine compound (21) is a cyclic azine compound represented by the following formula (23):

[0137] [ka]

[0138] During the ceremony, Ar 21 ~Ar 23 , n 21 , L 21 R has the same meaning as in the cyclic azine compound (21); Z 21 ~Z 25 are each independently C-Ar 23 , CR, or a nitrogen atom; Z 21 ~Z 25 Of these, two are nitrogen atoms; Z 21 ~Z 25 Of these, only one is C-Ar 23 is; Z 21 ~Z 25 Of these, Z 21 and X 25 Either one of them is C-Ar 23 If so, L 21 is a single bond, n 21 is 0 or 1; Z 21 ~Z 25 Among them, Z 22 ~Z 24One of the following is C-Ar 23 If so, L 21 is a phenylene group or a single bond, n 21 is 0, 1, or 2.

[0139] Cyclic azine compounds represented by formulae (24) to (27) The cyclic azine compound (21) is more preferably a cyclic azine compound represented by formula (24), (25), (26) or (27):

[0140] [ka]

[0141] During the ceremony, Ar 21 ~Ar 23 , n 21 , L 21 R has the same meaning as in the cyclic azine compound (21); Each V independently represents CR. That is, S 4 The number of ring nitrogen atoms in the ring is one.

[0142] Cyclic azine compounds represented by formulae (28) to (31) The cyclic azine compound (21) is more preferably a cyclic azine compound represented by formula (28), (29), (30) or (31):

[0143] [ka]

[0144] During the ceremony, Ar 21 ~Ar 23 , n 21 , L 21 R has the same meaning as in the cyclic azine compound (21); Each W independently represents CR. That is, S 5The number of ring nitrogen atoms in the ring is one or two.

[0145] L 21 is preferably a single bond.

[0146] The cyclic azine compound (21) has a higher crystallization temperature than conventionally known compounds due to the contribution of the meta-substituted pyridyl group and meta-substituted pyrimidyl group. As a result, the present inventors believe that the cyclic azine compound (21) has a high amorphous property when formed into a thin film. The present inventors speculate that when the cyclic azine compound (21) is used in an organic electroluminescent device, the effects of improving the driving stability and luminous efficiency of the organic electroluminescent device can be obtained due to the high amorphous property of the cyclic azine compound (21).

[0147] When the cyclic azine compounds (1), (11), and (21) are used as part of the components of an organic electroluminescent device (OLED; organic light emitting diode), they can provide effects such as high current efficiency and long life. In particular, when the cyclic azine compounds (1), (11), and (21) are used as an electron transport layer, these effects are more pronounced.

[0148] [Specific examples of cyclic azine compounds (1), (11), and (21)] Preferred examples of the fused ring compounds represented by cyclic azine compounds (1), (11), and (21) are shown in Tables 1-1 to 1-20, 2-1 to 2-10, and Tables 3-1 to 3-20, and Table 4-1 below, but the cyclic azine compounds (1), (11), and (21) are not limited to these compounds.

[0149] [Table 1-1]

[0150] [Table 1-2]

[0151]

Table 1-3

[0152]

Table 1-4

[0153]

Table 1-5

[0154]

Table 1-6

[0155]

Table 1-7

[0156]

Table 1-8

[0157]

Table 1-9

[0158]

Table 1-10

[0159]

Table 1-11

[0160]

Table 1-12

[0161]

Table 1-13

[0162]

Table 1-14

[0163]

Table 1-15

[0164]

Table 1-16

[0165]

Table 1-17

[0166]

Table 1-18

[0167]

Table 1-19

[0168]

Table 1-20

[0169]

Table 2-1

[0170]

Table 2-2

[0171]

Table 2-3

[0172] [Table 2-4]

[0173] [Table 2-5]

[0174] [Table 2-6]

[0175] [Table 2-7]

[0176] [Table 2-8]

[0177] [Table 2-9]

[0178] [Table 2-10]

[0179] Tables 2-1 to 2-10 show compounds having the skeletons (A1) to (H3) shown in Tables 1-1 to 1-20, and the substituents on the skeletons -Ar 3 , -Ar 4 is a group shown in Tables 2-1 to 2-10, (Xm-n) compounds. Here, X represents any alphabet selected from A to H. m represents any integer from 1 to 48, and n represents any integer from 1 to 237. In other words, the compound (Xm-n) represents the compounds (A1-1) to (H3-237). For example, a compound (B1-50) in which X=B, m=1, and n=50 has a skeleton of (B1), and the skeleton has a substituent -Ar 3 is a phenyl group, and -Ar 4 The following compound is shown, in which is a p-biphenyl group.

[0180] [ka]

[0181] The compounds represented by (B1-1) to (B1-48), (B2-1) to (B2-48), (B48-1) to (B48-48) respectively represent the same compounds having the corresponding skeleton of (A1). The compounds represented by (E1-1) to (E1-48), (E2-1) to (E2-48), (E36-1) to (E36-48) each represent the same compound as the corresponding compound having the skeleton of (D1). The compounds represented by (G2-1) to (G2-48) each represent the same compound as the corresponding compound having the skeleton of (G1). The compounds represented by (H2-1) to (H2-48) each represent the same compound as the corresponding compound having the skeleton of (H1).

[0182] [Table 3-1]

[0183] [Table 3-2]

[0184] [Table 3-3]

[0185] [Table 3-4]

[0186]

Table 3-5

[0187]

Table 3-6

[0188]

Table 3-7

[0189]

Table 3-8

[0190]

Table 3-9

[0191]

Table 3-10

[0192]

Table 3-11

[0193]

Table 3-12

[0194]

Table 3-13

[0195]

Table 3-14

[0196] [Table 3-15]

[0197] [Table 3-16]

[0198] [Table 3-17]

[0199] [Table 3-18]

[0200] [Table 3-19]

[0201] [Table 3-20]

[0202] [Table 4-1]

[0203] Table 4-1 shows compounds having the skeletons (I1) to (I314) shown in Tables 3-1 to 3-20, and the substituents -Ar 23 represents a compound of (Ip-q), which is a group shown in Table 4-1. Here, p is any integer from 1 to 314, and q is any integer from 1 to 12. That is, the compound (Ip-q) refers to the compounds (I1-1) to (I314-12). For example, in the case of a compound (I3-3) in which p=3 and q=3, the compound has a skeleton of (I4), and the skeleton has a substituent -Ar 23The following compound is shown, in which the aryl group is a 9-phenanthryl group.

[0204] [ka]

[0205] The uses of the cyclic azine compounds (1), (11), and (21) will be described below. <Materials for organic electroluminescence devices, electron transport materials for organic electroluminescence devices> The cyclic azine compounds (1), (11), and (21) can be used, for example, as a material for an organic electroluminescent device, although they are not particularly limited thereto. The cyclic azine compounds (1), (11), and (21) can be used, for example, as an electron transport material for an organic electroluminescent device. That is, the material for organic electroluminescence elements according to one embodiment of the present invention contains cyclic azine compounds (1), (11), and (21). Also, the electron transport material for organic electroluminescence elements according to one embodiment of the present invention contains cyclic azine compounds (1), (11), and (21). The material for organic electroluminescence elements and the electron transport material for organic electroluminescence elements containing the cyclic azine compounds (1), (11), and (21) contribute to the production of organic electroluminescence elements having excellent durability and current efficiency.

[0206] <Organic electroluminescent device> An organic electroluminescent device according to one embodiment of the present invention includes cyclic azine compounds (1), (11), and (21). The configuration of the organic electroluminescent device is not particularly limited, but examples thereof include the following configurations (i) to (vi). (i): Anode / Emitting layer / Cathode (ii): anode / hole transport layer / light emitting layer / cathode (iii): anode / light-emitting layer / electron transport layer / cathode (iv): anode / hole transport layer / light emitting layer / electron transport layer / cathode (v): anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (vi): Anode / hole injection layer / charge generation layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0207] Hereinafter, an organic electroluminescence device according to an embodiment of the present invention will be described in more detail by taking the above-mentioned configuration (vi) as an example with reference to Fig. 1. Fig. 1 is a schematic cross-sectional view showing an example of a layered configuration of an organic electroluminescence device containing a cyclic azine compound according to an embodiment of the present invention. 1 has a so-called bottom-emission type element configuration, the organic electroluminescence element according to one embodiment of the present invention is not limited to the bottom-emission type element configuration. That is, the organic electroluminescence element according to one embodiment of the present invention may have a top-emission type element configuration or another known element configuration.

[0208] The organic electroluminescent device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a charge generation layer 4, a hole transport layer 5, a light emitting layer 6, an electron transport layer 7, and a cathode 8 in this order. However, some of these layers may be omitted, or other layers may be added. For example, an electron injection layer may be provided between the electron transport layer 7 and the cathode 8, or the charge generation layer 4 may be omitted, and the hole transport layer 5 may be provided directly on the hole injection layer 3. Alternatively, a single layer having the functions of the multiple layers, such as an electron injection / transport layer having the functions of both the electron injection layer and the electron transport layer in a single layer, may be provided instead of the multiple layers. Furthermore, for example, the single-layer hole transport layer 5 and the single-layer electron transport layer 7 may each be made up of multiple layers.

[0209] [Layer containing cyclic azine compounds represented by formula (11) and formula (1)] The organic electroluminescent device contains the cyclic azine compounds represented by the above formula (11) and formula (1) in at least one layer selected from the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode. Therefore, in the configuration example shown in FIG. 1, the organic electroluminescent device 100 contains the cyclic azine compounds (1), (11), and (21) in at least one layer selected from the group consisting of the light-emitting layer 6 and the electron transport layer 7. In particular, it is preferable that the electron transport layer 7 contains the cyclic azine compounds (1), (11), and (21). The cyclic azine compounds (1), (11), and (21) may be contained in multiple layers of the organic electroluminescent device, and when an electron injection layer is provided between the electron transport layer and the cathode, the electron injection layer may contain the cyclic azine compounds (1), (11), and (21). In the following, an organic electroluminescent device 100 in which the electron transport layer 7 contains the cyclic azine compounds (1), (11), and (21) will be described.

[0210] [Substrate 1] There is no particular limitation on the substrate, and examples thereof include a glass plate, a quartz plate, a plastic plate, etc. In addition, in the case of a configuration in which light emission is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

[0211] Examples of light-transmitting plastic films include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

[0212] [Anode 2] An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side). In the case of an organic electroluminescent device in which light is emitted through the anode, the anode is formed from a material that is transparent or substantially transparent to the emitted light.

[0213] The transparent material used for the anode is not particularly limited, but examples thereof include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, aluminum-doped tin oxide, magnesium indium oxide, nickel tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide. In the case of an organic electroluminescent device in which light is extracted only from the cathode side, the transmittance characteristics of the anode are not important. Therefore, examples of materials that can be used for the anode in this case include gold, iridium, molybdenum, palladium, platinum, etc. A buffer layer (electrode interface layer) may be provided on the anode.

[0214] [Hole injection layer 3, hole transport layer 5] Between the anode 2 and a light-emitting layer 6 described later, a hole injection layer 3, a charge generation layer 4 described later, and a hole transport layer 5 are provided in this order from the anode 2 side. The hole injection layer and the hole transport layer have the function of transporting holes injected from the anode to the light-emitting layer. By interposing this hole injection layer and hole transport layer between the anode and the light-emitting layer, a large number of holes can be injected into the light-emitting layer with a lower electric field.

[0215] The hole injection layer and the hole transport layer also function as electron barrier layers. That is, the electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light emitting layer are prevented from leaking to the hole injection layer and / or the hole transport layer due to the electron barrier present at the interface between the light emitting layer and the hole injection layer and / or the hole transport layer. As a result, the electrons are accumulated at the interface in the light emitting layer, which brings about effects such as improved current efficiency, and an organic electroluminescent device with excellent light emitting performance is obtained.

[0216] The material for the hole injection layer and the hole transport layer has at least one of hole injection property, hole transport property, and electron barrier property. The material for the hole injection layer and the hole transport layer may be either an organic material or an inorganic material.

[0217] Specific examples of materials for the hole injection layer and the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds, etc. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred.

[0218] Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- Examples of such compounds include di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA). Furthermore, inorganic compounds such as p-type Si and p-type SiC can also be given as examples of materials for the hole injection layer and the hole transport layer.

[0219] The hole injection layer and the hole transport layer may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0220] [Charge generation layer 4] Between the hole injection layer 3 and the hole transport layer 5, a charge generation layer 4 may be provided. The material for the charge generating layer is not particularly limited, but may be, for example, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN). The charge generating layer may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0221] [Light-emitting layer 6] The light-emitting layer 6 is provided between the hole transport layer 5 and the electron transport layer 7 described below. Examples of materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs are recombined, resulting in light emission.

[0222] The light-emitting layer may consist of a single small molecule or single polymeric material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from the dopant and can be of any color.

[0223] Examples of the host material include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, examples of the compound include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, and the like.

[0224] Examples of the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium, thiapyrylium compound, fluorene derivative, periflanthene derivative, indenoperylene derivative, bis(azinyl)amine boron compound, bis(azinyl)methane compound, carbostyril compound, etc. The fluorescent dopant may be a combination of two or more selected from these.

[0225] Phosphorescent dopants include, for example, organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0226] Specific examples of fluorescent dopants and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))).

[0227] In addition, the light-emitting material is not limited to being contained only in the light-emitting layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (hole transport layer 5 or electron transport layer 7). This can further increase the current efficiency of the organic electroluminescent device.

[0228] The light-emitting layer may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same composition or different compositions.

[0229] [Electron transport layer 7] An electron transport layer 7 is provided between the light emitting layer 6 and a cathode 8 which will be described later. The electron transport layer has a function of transporting electrons injected from the cathode to the light emitting layer. By interposing the electron transport layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a lower electric field.

[0230] As described above, the electron transport layer preferably contains the cyclic azine compounds represented by the above formulas (11) and (1).

[0231] The electron transport layer may further contain a conventionally known electron transport material in addition to the cyclic azine compounds (1), (11), and (21). Examples of conventionally known electron transport materials include 8-hydroxyquinolinato lithium (Liq), bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, and bis(2-methyl-8-quinolinato)-1-naphthol. bis(2-methyl-8-quinolinato)-2-naphtholatogallium, 2-[3-(9-phenanthrenyl)-5-(3-pyridinyl)phenyl]-4,6-diphenyl-1,3,5-triazine, and 2-(4,''-di-2-pyridinyl[1,1':3',1''-terphenyl]-5-yl)-4,6-diphenyl-1,3,5-triazine, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-quinolinato)-4-(phenylphenolato)aluminum), and bis(10-hydroxybenzo[h]quinolinato)beryllium).

[0232] The electron transport layer may have a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions. When the electron transport layer has a two-layer structure in which a first electron transport layer is on the light-emitting layer side and a second electron transport layer is on the cathode side, it is preferable that the second electron transport layer contains a cyclic azine compound (1), (11), or (21).

[0233] [Cathode 8] A cathode 8 is provided on the electron transport layer 7 . In the case of an organic electroluminescence element having a configuration in which only light emitted through the anode is extracted, the cathode can be formed from any conductive material. Cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, indium, lithium / aluminum mixtures, rare earth metals, etc. A buffer layer (electrode interface layer) may be provided on the cathode (on the electron transport layer side).

[0234] [How each layer is formed] Each layer except for the electrodes (anode, cathode) described above can be formed by forming the material of each layer (together with a material such as a binder resin and a solvent, if necessary) into a thin film by a known method such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett method (LB method). There are no particular limitations on the film thickness of each layer thus formed, and it can be appropriately selected depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0235] The anode and cathode can be formed by forming a thin film of an electrode material by a method such as vapor deposition, sputtering, etc. A pattern may be formed through a mask having a desired shape during vapor deposition or sputtering, or a pattern having a desired shape may be formed by photolithography after forming a thin film by vapor deposition, sputtering, etc.

[0236] The film thickness of the anode and cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0237] The organic electroluminescent device according to one embodiment of the present invention may be used as a kind of lamp for illumination or exposure light source, or as a projection device for projecting an image, or as a display device for directly viewing still images or moving images. When used as a display device for playing moving images, the driving method may be either a passive matrix method or an active matrix method. In addition, a full-color display device can be produced by using two or more kinds of organic electroluminescent devices according to this embodiment having different emission colors.

[0238] The cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention can be synthesized by appropriately combining known reactions (for example, Suzuki-Miyaura cross-coupling reaction, etc.). EXAMPLES

[0239] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples in any way.

[0240] 1 H-NMR measurements were performed using Gemini200 (Varian). FDMS measurements were carried out using a Hitachi M-80B. The glass transition temperature was measured using a DSC7020 (manufactured by Hitachi High-Tech Science Corporation). The light-emitting characteristics of the organic electroluminescent device were evaluated by applying a direct current to the fabricated device at room temperature using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse Corporation).

[0241] Synthesis Example 1

[0242] [ka]

[0243] Under an argon stream, 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3,5-triazine (5.00 g, 11.49 mmol), 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine (5.84 g, 12.63 mmol), and tetrakis(triphenylphosphine)palladium (0.40 g, 0.345 mmol) were dissolved in tetrahydrofuran (100 mL). To this was added 2M aqueous potassium carbonate solution (18 mL, 36 mmol), and the mixture was stirred at 75°C for 26 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), ethanol (50 mL), and hexane (50 mL). This solid was suspended in toluene (250 mL), stirred at 125°C, and then allowed to cool. The precipitated solid was filtered off, and the resulting solid was dissolved in 500 mL of toluene. Activated carbon was added to the solution, stirred, filtered through Celite, and the filtrate was concentrated under reduced pressure. The concentrated solution was dried to obtain the target white solid of 2-(3'-{6-[(1,1'-biphenyl)-4-yl]-4-phenylpyridin-2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (Compound B1-50) (yield: 6.46 g, 81%).

[0244] 1 H-NMR (CDCl 3)δ(ppm):7.39(t,J=7.2Hz,1H),7.47-7.53(m,3H),7.55-7.72(m,11H),7.77-7.82(m,5H),7.94(d,J=8.5Hz,2H), 8.00(s,2H),8.26(d,J=7.6Hz,1H),8.33(d,J=8.7Hz,2H),8.57(s,1H),8.81-8.84(m,4H),8.91(d,J=8.6Hz,2H). The glass transition temperature of compound B1-50 was 116°C.

[0245] Synthesis Example 2

[0246] [ka]

[0247] The same experimental procedure as in Synthesis Example 1 was carried out except that 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was used instead of 2-(3-bromophenyl)-6-(4-chlorophenyl)-4-phenylpyridine, and the target 2-{3'-[6-(4-chlorophenyl)-4-phenylpyridyl-2-yl]-1,1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine was obtained as a white solid (yield 6.00 g, 92%).

[0248] [ka]

[0249] Under a nitrogen atmosphere, 4,6-diphenyl-2-{3'-[6-(4-chlorophenyl)-4-phenylpyridyl-2-yl]-biphenyl-4-yl}-1,3,5-triazine (6.00 g, 9.25 mmol), 3-pyridylboronic acid (1.3726 g, 11.10 mmol), and 0.05 M Pd(OAc) were added. 2 / Xphos THF solution 4.7ml, K 2 CO 317 mL of aqueous solution and THF (100 mL) were added and stirred at 70°C for 1 day. After the reaction, the mixture was allowed to cool to room temperature, and the precipitated solid was collected by filtration. The obtained solid was recrystallized (toluene / hexane) and recrystallized (chlorobenzene / hexane) to obtain the target white solid of 2-(3'-{4-phenyl-6-[4-(3-pyridyl)phenyl]pyridyl-2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (compound B1-75) (yield: 2.67 g, 42%).

[0250] 1 H-NMR (CDCl 3 )δ(ppm):7.41(dd,1H),7.69-7.51(m,10H),7.82-7.77(m,5H),7.94(dd,2H),7.98(dt,1H),8.00(dd ,2H),8.25(d,1H),8.37(d,2H),8.56(t,1H),8.63(dd,1H),8.81(dd,4H),8.91(d,2H),8.96(d,1H). The glass transition temperature of compound B1-75 was 120°C.

[0251] Synthesis Example 3

[0252] [ka]

[0253] The same experimental procedure as in Synthesis Example 1 was carried out except that 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was replaced with 4-(3-bromophenyl)-2-(1-naphthyl)-6-phenylpyridine, and the target 2-{3'-[2-(1-naphthyl)-6-phenylpyridyl-4-yl]-1,1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (C1-57) was obtained as a white solid (yield 4.4 g, 53%).

[0254] 1 H-NMR (CDCl 3)δ(ppm):7.47-7.62(m,5H),7.66-7.76(m,8H),7.88(d,J=7.2Hz,1H),7.97(d,J=8.0Hz,1H),8.05-8.13(m,4H), 8.16(d,J=8.6Hz,2H),8.28-8.34(m,3H),8.43(s,1H),8.47(s,1H),8.77(d,J=6.9Hz,4H),8.86(d,J=8.6Hz,2H). The glass transition temperature of compound C1-57 was 114°C.

[0255] Synthesis Example 4

[0256] [ka]

[0257] The same experimental procedure as in Synthesis Example-1 was carried out except that 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was used instead of 2-(3-bromophenyl)-4-(1-naphthyl)-6-phenylpyridine, and the target 2-{3'-[4-(1-naphthyl)-6-phenylpyridyl-2-yl]-1,1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (A1-57) was obtained as a white solid (yield 5.2 g, 73%).

[0258] 1 H-NMR(CDCl3)δ(ppm):7.74-7.72(m,14H),7.73(d,J=8.1Hz,1H),7.83-7.87(m,4H),7.91(d ,J=7.8Hz,3H),8.16-8.20(m,3H),8.50(s,1H),8.74(d,J=6.4Hz,4H),8.82(d,J=8.5Hz,2H). The glass transition temperature of compound A1-57 was 116°C.

[0259] Synthesis Example 5

[0260] [ka]

[0261] The same experimental procedure as in Synthesis Example-1 was carried out except that 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was used instead of 2-[(1,1'-biphenyl)-4-yl]-4-(3-bromophenyl)-2-phenylpyridine, and the target 2-(3'-{6-phenyl-2-[(1,1'-biphenyl)-4-yl]pyridin-2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (C1-50) was obtained as a white solid (yield 3.0 g, 69%).

[0262] 1 H-NMR(CDCL3)δ(ppm):7.39(t,J=7.3Hz,1H),7.46-7.71(m,14H),7.76-7.85(m,4H),7.91(d,J=8.4Hz,2H),8.01(d,J =12.5Hz,2H),8.07(s,1H),8.26(d,J=7.2Hz,2H),8.33(d,J=8.4Hz,2H),8.82(d,J=6.5Hz,4H),8.91(d,J=8.3Hz,2H).

[0263] Synthesis Example 6

[0264] [ka]

[0265] 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was changed to 2-[(1,1'-biphenyl)-4-yl]-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine, and 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3,5- The same experimental procedure as in Synthesis Example-1 was carried out except that triazine was changed to 3-(2,6-diphenyl-4-pyridyl)phenylboronic acid, and the target 2-(3'-(2,6-diphenylpyridin-4-yl}-1,1'-biphenyl-4-yl)-4-(1,1'-biphenyl)-6-phenyl-1,3,5-triazine (C2-1) was obtained as a white solid (yield 22.2 g, 74%).

[0266] 1 H-NMR (CDCl 3 )δ(ppm):7.41-7.56(m,9H),7.59-7.74(m,6H),7.79-7.84(m,4H),7.90(d,J=8.3Hz,2H), 7.98(s,2H),8.06(s,1H),8.25(d,J=7.5Hz,4H),8.23(d,J=6.5Hz,2H),8.87-8.93(m,4H). The glass transition temperature of compound C2-1 was 121°C.

[0267] Synthesis Example 7

[0268] [ka]

[0269] 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was changed to 2-[(1,1'-biphenyl)-4-yl]-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine, and 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3,5- The same experimental procedure as in Synthesis Example-1 was carried out except that triazine was changed to 3-(4,6-diphenyl-2-pyridyl)phenylboronic acid, and the target 2-(3'-(4,6-diphenylpyridin-2-yl}-1,1'-biphenyl-4-yl)-4-(1,1'-biphenyl)-6-phenyl-1,3,5-triazine (A2-1) was obtained as a white solid (yield 5.39 g, 55%).

[0270] 1 H-NMR(CDCl3)δ(ppm):7.43-7.71(m,13H),7.76(d,J=7.2Hz,2H),7.80-7.87(m,5H),7.95-8.01(m,4H), 8.27(d,J=8.1Hz,3H),8.57(s,1H),8.86(d,J=8.1Hz,2H),8.91(d,J=8.6Hz,2H),8.94(d,J=8.6Hz,2H).

[0271] Synthesis Example 8

[0272] [ka]

[0273] 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was replaced with 4-(4-bromophenyl)-2,6-diphenyl-1,3,5-triazine, and 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3,5-triazine was replaced with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl. The same experimental procedure as in Synthesis Example-1 was carried out except that 2-[(3″-(2,6-diphenylpyridin-4-yl)-1,1′:3′:1″-terphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (F13-1) was changed to a white solid (yield 13.5 g, 76%).

[0274] 1 H-NMR(CDCl3)δ(ppm):7.43-7.81(m,18H),7.89(d,8.4Hz,2H),7.97(s,2H),8. 00(d,13.2Hz,2H),8.23(d,7.1Hz,4H),8.81(d,6.5Hz,4H),8.89(d,8.6Hz,2H).

[0275] Synthesis Example 9

[0276] [ka]

[0277] 2-[(1,1'-biphenyl)-4-yl]-6-(3-bromophenyl)-4-phenylpyridine was changed to 2-(3'''-chloro-1,1':4',1'':3'',1'''-quaterphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine, and 2-{4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]}-4,6-diphenyl-1,3 The same experimental procedure as in Synthesis Example 1 was carried out except that 3-(2,6-diphenyl-4-pyridyl)phenylboronic acid was used instead of ,5-triazine, and the target 2-[(3'''-(2,6-diphenylpyridin-4-yl)-1,1':4',1'':3'',1'''-quaterphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (G3-1) was obtained as a white solid (yield 4.2 g, 79%).

[0278] 1 H-NMR (CDCl 3 )δ(ppm):7.44-7.73(m,16H),7.76-7.89(m,8H),7.95(s,1H),7.97(s,2H),8. 01(s,1H),8.23(d,J=7.1Hz,4H),8.81(d,J=6.4Hz,4H),8.88(d,J=8.6Hz,2H).

[0279] Synthesis Example 1

[0280] [ka]

[0281] Under an argon stream, 2-[3'-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-yl}]-4,6-diphenyl-1,3,5-triazine (2.05 g, 4.0 mmol), 2-bromo-6-chloropyridine (2.31 g, 12.0 mmol), and tetrakis(triphenylphosphine)palladium (0.139 g, 0.12 mmol) were dissolved in tetrahydrofuran (20 mL). To this was added 2M potassium carbonate aqueous solution (6 mL, 12 mmol), and the mixture was stirred at 75°C for 4 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), methanol (50 mL), and hexane (50 mL). The solid was suspended in toluene (50 mL), stirred at 120°C, and then cooled. The precipitated solid was filtered off and washed with toluene (5 mL) and methanol (50 mL) to obtain the desired 4,6-diphenyl-2-[3'-(2-chloropyridin-6-yl)-1,1'-biphenyl-4-yl]-1,3,5-triazine as a white solid (yield 1.35 g, 68%).

[0282] 1 H-NMR (CDCl 3 )δ(ppm):8.88(d,J=8.0Hz,2H),8.81(dd,J 1 =8.0Hz,J 2 =1.6Hz,4H),8.34(t,J=1.6Hz,1H),8.03(d,J=8.0Hz,1H),7.88(d,J=8.0Hz,2H),7.77-7.75(m,2H),7.64-7.58(m,9H)

[0283] Synthesis Example 10

[0284] [ka]

[0285] Under an argon atmosphere, 4,6-diphenyl-2-[3'-(2-chloropyridin-6-yl)-1,1'-biphenyl-4-yl]-1,3,5-triazine (1.35g, 2.7mmol) obtained in Synthesis Example-1, 9-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)phenanthrene (2.37g, 8.2mmol), palladium acetate (6.11mg, 0.03mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (38.9mg, 0.08mmol; X-Phos) were dissolved in tetrahydrofuran (14mL). 2M tripotassium phosphate aqueous solution (4mL, 8.1mmol) was added to the mixture, which was then stirred at 75°C for 3 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL), methanol (50 mL), and hexane (50 mL). The solid was suspended in toluene (80 mL), stirred at 120° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (5 mL) and methanol (50 mL) to obtain the desired white solid of 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-6-yl}-1,1'-biphenyl-4-yl]-1,3,5-triazine (compound I171-3) (yield: 1.58 g, 91%).

[0286] 1 H-NMR (CDCl 3 )δ(ppm):8.86(d,J=8.7Hz,2H),8.83-8.79(m,5H),8.77(d,J=8.7Hz,1H),8.47(s,1H),8.28(d,J=8.4Hz,1H ),8.18(d,J=7.8Hz,1H),8.00-7.91(m,4H),7.89(d,J=8.1Hz,2H),7.77(d,J=7.7Hz,1H),7.74-7.57(m,12H) The glass transition temperature of compound I171-3 was 118°C.

[0287] Synthesis Example 2

[0288] [ka]

[0289] Under an argon stream, 2-[3'-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-yl}]-4,6-diphenyl-1,3,5-triazine (12.79 g, 25.0 mmol), 4-bromo-2-chloropyridine (14.43 g, 75.0 mmol), and tetrakis(triphenylphosphine)palladium (0.867 g, 0.75 mmol) were dissolved in tetrahydrofuran (125 mL). To this was added 2M aqueous potassium carbonate solution (37.5 mL, 75 mmol), and the mixture was stirred at 75°C for 13 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (200 mL), methanol (100 mL), and hexane (100 mL). This solid was suspended in toluene (550 mL), stirred at 120° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (20 mL) and methanol (100 mL) to obtain the target white solid of 4,6-diphenyl-2-[3'-(2-chloropyridin-4-yl)-1,1'-biphenyl-4-yl]-1,3,5-triazine (yield: 11.6 g, 93%).

[0290] 1 H-NMR (CDCl 3 ) δ(ppm):8.89(dd,J 1 =6.4Hz,J 2 =1.6Hz,2H),8.83-8.80(m,4H),8.49(d,J=2.4Hz,1H),7.53(t,J=1.6Hz,1H),7.84(dd,J 1 =6.4Hz,J 2 =1.6Hz,2H),7.80(dt,J 1 =6.4Hz,J 2 =1.6Hz,1H),7.65-7.59(m,9H),7.53(dd,J 1 =4.8Hz,J 2 =1.6Hz,1H)

[0291] Synthesis Example 11

[0292] [ka]

[0293] Under an argon atmosphere, 4,6-diphenyl-2-[3'-(2-chloropyridin-4-yl)-1,1'-biphenyl-4-yl]-1,3,5-triazine (6.21g, 12.5mmol) obtained in Synthesis Example-2, 9-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)phenanthrene (10.9g, 37.5mmol), palladium acetate (28.06mg, 0.13mmol), and X-Phos (178.77mg, 0.38mmol) were dissolved in tetrahydrofuran (160mL). To this was added 2M tripotassium phosphate aqueous solution (19mL, 37.5mmol), and the mixture was stirred at 75°C for 3 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (200 mL), methanol (200 mL), and hexane (200 mL). The solid was suspended in toluene (1000 mL), stirred at 120° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (30 mL) and methanol (200 mL) to obtain the target white solid of 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-4-yl}1,1'-biphenyl-4-yl]-1,3,5-triazine (compound I179-3) (yield: 6.92 g, yield: 86.7%).

[0294] 1 H-NMR (CDCl 3 )δ(ppm):8.93(d,J=6.4Hz,1H),8.88(dd,J 1 =6.4Hz,J 2 =1.6Hz,2H),8.81-8.79(m,6H),8.76(d,J=8.0Hz,1H),8.18(d,J=6.4Hz,1H),8.04(t,J=1 .6Hz,1H),7.98-7.96(m,4H),7.87(d,J=8.0Hz,2H),7.82-7.77(m,2H),7.66-7.59(m,10H) Compound I179-3 had a glass transition temperature of 120°C, a crystallization temperature of 182°C, and a melting point of 246°C.

[0295] Synthesis Example 3

[0296] [ka]

[0297] Under an argon stream, 2-bromo-4-chloropyridine (0.679 g, 3.53 mmol), 5,5-dimethyl-2-(9-phenanthrenyl)-1,3,2-dioxaborilane (1.02 g, 3.53 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.122 g, 0.106 mmol) were dissolved in tetrahydrofuran (30 mL). To this was added 2.0 M aqueous potassium carbonate solution (5.3 mL, 10.6 mmol), and the mixture was stirred at 65°C for 24 hours. After cooling to room temperature, the mixture was separated with water and methylene chloride. The obtained organic layer was concentrated to dryness to obtain the desired 4-chloro-2-(9-phenanthrenyl)pyridine as a yellowish white solid (yield 0.978 g, 96%).

[0298] Synthesis Example 12

[0299] [ka]

[0300] Under an argon stream, 2-[3'-{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-yl}]-4,6-diphenyl-1,3,5-triazine (1.25 g, 2.98 mmol), 3-chloro-5-(9-phenanthrenyl)pyridine (0.949 g, 3.28 mmol) obtained in Synthesis Example-3, palladium acetate (20.0 mg, 89.1 μmol), and X-Phos (85.1 mg, 0.179 mmol) were dissolved in tetrahydrofuran (30 mL). To this was added 2.0 M aqueous potassium phosphate solution (4.5 mL, 8.93 mmol), and the mixture was stirred at 50° C. for 3 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water and methanol. This solid was suspended in toluene (250 mL), stirred at 125° C., and then allowed to cool. The resulting solid was recrystallized from toluene to obtain the target white solid of 4,6-diphenyl-2-[3'-{5-(9-phenanthrenyl)pyridin-3-yl}-1,1'-biphenyl-4-yl]-1,3,5-triazine (compound I187-3) (yield: 1.37 g, 72%).

[0301] 1 H-NMR (CDCl 3 )δ(ppm):9.06(d,J=2.3Hz,1H),8.88(d,J=8.7Hz,2H),8.85(d,J=1.8 Hz,1H),8.81-8.76(m,5H),8.18(d,J=2.3Hz,1H),7.99(s,1H),7.94(dd,J=12.1,7.5Hz,2H),7.87(d,J=8.7 Hz, 2H), 7.80-7.71 (m, 5H), 7.69-7.58 (m, 10H). The glass transition temperature of compound I187-3 was 124°C.

[0302] Synthesis Example 13

[0303] [ka]

[0304] Under an argon atmosphere, 2-{3-(trifluoromethanesulfonyloxy)phenyl}-4,6-bis([1,1'-biphenyl]-4-yl)triazine (4.00g, 6.56mmol), 3-(phenanthren-9-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (3.25g, 8.53mmol), palladium acetate (0.04g, 0.16mmol) and X-Phos (0.16g, 0.33mmol) were dissolved in tetrahydrofuran (50mL). 4M aqueous potassium phosphate solution (2.5mL, 9.97mmol) was added to the solution, and the mixture was stirred at 65°C for 4 hours. Water (50ml) was added, and the mixture was allowed to cool to room temperature, and the precipitated solid was filtered off. The solid obtained was washed with water (50mL) and ethanol (50mL). This solid was suspended in ethyl acetate (50 mL), stirred at 75°C, and allowed to cool. The precipitated solid was filtered off, and the resulting solid was dissolved in 300 mL of chlorobenzene. The insoluble matter was filtered off, and the filtrate was distilled off under reduced pressure. Ethanol (50 ml) was added, and the precipitated solid was filtered off by stirring, and the resulting solid was washed with hexane. The solid was dissolved again in chlorobenzene (300 ml), and activated carbon was added to the solution and stirred, and the solution was filtered through a Kiriyama funnel lined with silica gel and Celite, and the filtrate was distilled off under reduced pressure. The concentrated liquid was dried to obtain the desired white solid of 4,6-bis[(1,1'-biphenyl)-4-yl]-2-{[5-(phenanthren-9-yl)pyridin-3-yl]-phenyl-3-yl}-1,3,5-triazine (compound I27-3) (yield 1.7 g, 36%).

[0305] 1 H-NMR (CDCl 3 )δ(ppm):9.17-9.10(m,2H),8.92-8.82(m,7H),8.78(d,J=8.6Hz,1H),8.26(m,1H),8.03-7.9 2(m,3H),7.85-7.79(m,5H),7.79-7.61(m,9H),7.51(t,J=7.2Hz,4H),7.42(t,J=7.6Hz,2H). Compound I27-3 had a glass transition temperature of 136°C, a crystallization temperature of 201°C, and a melting point of 255°C.

[0306] Synthesis Example 4

[0307] [ka]

[0308] Under an argon stream, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (7.50 g, 17.2 mmol), 2-chloro-4-iodo-3-methylpyridine (4.80 g, 19.0 mmol), and tetrakis(triphenylphosphine)palladium (0.597 g, 0.52 mmol) were dissolved in tetrahydrofuran (250 mL). To this was added 2M potassium carbonate aqueous solution (25.8 mL, 52 mmol), and the mixture was stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated with water and methylene chloride. The obtained organic layer was concentrated to dryness to obtain a yellow solid. This solid was suspended in toluene (10 mL), stirred at 120°C, and then cooled. The precipitated solid was filtered off and washed with toluene (5 mL) and ethanol (10 mL) to obtain the desired 2-[3-(2-chloro-3-methylpyridin-4-yl)phenyl]-4,6-diphenyl-1,3,5-triazine as a yellow solid (yield 2.8 g, 37%).

[0309] 1 H-NMR (CDCl 3 )δ(ppm):8.87-8.70(m,6H),8.34(d,J=4.8Hz,1H),7.72-7.53(m,9H),2.41(s,3H)

[0310] Synthesis Example 14

[0311] [ka]

[0312] Under an argon stream, 2-[3-(2-chloro-3-methylpyridin-4-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (2.75 g, 6.32 mmol) obtained in Synthesis Example-4, 9-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)phenanthrene (2.20 g, 7.59 mmol), and tetrakis(triphenylphosphine)palladium (219.2 mg, 0.19 mmol) were dissolved in tetrahydrofuran (65 mL). To this was added 2M aqueous potassium carbonate solution (9.5 mL, 21.6 mmol), and the mixture was stirred at 70° C. for 13 hours. After cooling to room temperature, water (300 mL) was added, and the precipitated solid was filtered off. The obtained solid was washed with water (100 mL) and ethanol (200 mL). This solid was suspended in toluene (100 mL), stirred at 120° C., and then allowed to cool. The precipitated solid was filtered off and washed with toluene (10 mL) and ethanol (50 mL) to obtain the target white solid of 2,4-diphenyl-6-[3-(3-methyl-2-phenanthrenylpyridin-4-yl)phenyl]-1,3,5-triazine (Compound I141-3) (yield: 2.56 g, 70.2%).

[0313] 1 H-NMR (CDCl 3 )δ(ppm):8.87-8.77(m,8H),8.75(d,J=4.4Hz,1H),7.95(d,J=8.9Hz,1H),7.85(s,1H),7.56-7.73(m,13H),7.44(d,J=5.6Hz,1H),2.12(s,3H) Compound I141-3 had a glass transition temperature of 134°C, a crystallization temperature of 215°C, and a melting point of 268°C.

[0314] Synthesis Example 5

[0315] [ka]

[0316] Under an argon atmosphere, 3-bromo-6-hydroxy-2-methylpyridine (5.23 g, 27.8 mmol), 5,5-dimethyl-2-phenanthrenyl-1,3,2-dioxaborinane (9.69 g, 33.4 mmol), palladium acetate (187 mg, 0.83 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (385 mg, 1.67 mmol; S-Phos) were suspended in tetrahydrofuran (93 mL), and 3M potassium phosphate aqueous solution (28 mL) was added. This mixture was stirred at 80°C for 21 hours, then cooled to room temperature, and chloroform and water were added to the reaction mixture. After separating the organic layer, the aqueous layer was extracted twice with chloroform. The organic layers were combined and dried over sodium sulfate, and the solid was filtered off, and the low boiling point fraction was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: hexane / ethyl acetate) to obtain 6-hydroxy-2-methyl-3-phenanthrenylpyridine (yield: 3.58 g, 45%).

[0317] 1 H-NMR (CDCl 3 )δ(ppm):12.63(s,1H),8.80(d,J=8.2Hz,1H),8.74(d,J=8.2Hz,1H),7.91(dd,J=7.8Hz,1.3Hz,1H),7.74-7 .63(m,5H),7.59(ddd,J=8.2Hz,6.9Hz,1.2Hz,1H),7.46(d,J=9.2Hz,1H),6.59(d,J=9.2Hz,1H),2.21(s,3H)

[0318] Synthesis Example 6

[0319] [ka]

[0320] Under an argon atmosphere, 6-hydroxy-2-methyl-3-phenanthrenylpyridine (1.91 g, 6.7 mmol) obtained in Synthesis Example 5 was dissolved in dichloromethane (54 mL), and pyridine (0.81 mL, 10.1 mmol) was added. The mixture was cooled to 0°C, and then trifluoromethanesulfonic anhydride (1.65 mL, 10.1 mmol; Tf 2 O) was added. The mixture was warmed to room temperature and stirred for 16 hours, after which chloroform and water were added to the reaction mixture. The organic layer was separated, and the aqueous layer was extracted twice with chloroform. The organic layers were combined and dried over sodium sulfate, after which the solid was filtered off and the low boiling point fraction was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography to give {3-(9-phenanthrenyl)-2-methylpyridin-6-yl}trifluoromethanesulfonate (2.77 g, 99%).

[0321] 1 H-NMR (CDCl 3 )δ(ppm):8.81(d,J=8.3Hz,1H),8.76(d,J=8.2Hz,1H),7.91(dd,J=7.8Hz,1.2Hz,1H),7.81(d,J=8.1Hz,1H),7.76-7.69(m,2H),7.67(ddd, J=7.4Hz,7.4Hz,1.2Hz,1H),7.62(s,1H),7.56(ddd,J=8.2Hz,7.0Hz,1.2Hz,1H),7.38(d,J=8.2Hz,1H),7.16(d,J=8.2Hz,1H),2.30(s,3H)

[0322] Synthesis Example 15

[0323] [ka]

[0324] Under an argon atmosphere, {3-(9-phenanthrenyl)-2-methylpyridin-6-yl}trifluoromethanesulfonate obtained in Synthesis Example-6, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (2.77 g, 6.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (193 mg, 0.18 mmol) were suspended in tetrahydrofuran (28 mL). 2.0 M potassium carbonate aqueous solution (25 mL) was added to the suspension and stirred at 80° C. for about 14 hours. After cooling to room temperature, the solvent was removed under reduced pressure, and water and methanol were added. The precipitated solid was filtered and washed with water (50 mL) and methanol (50 mL). The obtained solid was dissolved in toluene (200 mL). Activated carbon was added to this solution, and the mixture was stirred, filtered through Celite, and the filtrate was concentrated under reduced pressure. The crude product was recrystallized from toluene to obtain the target compound 2,4-diphenyl-6-[3-(2-methyl-3-phenanthrenylpyridin-6-yl)phenyl]-1,3,5-triazine (compound I153-3) (1.87 g, 58%).

[0325] 1 H-NMR (CDCl 3 )δ(ppm):9.45(t,J=1.6Hz,1H),8.88(ddd,J=7.8,Hz,1.4Hz,1.4Hz,1H),8.86-8.81(m,5H),8.79(d,J=8.0Hz,1H),8.44(ddd,J=7.8 Hz,1.8Hz,1.2Hz,1H),7.94(dd,J=7.8Hz,1.3Hz,1H),7.93(d,J=7.8Hz,1H),7.80(d,J=7.8Hz,1H),7.78-7.55(m,13H),2.46(s,3H) The glass transition temperature of compound I153-3 was 122°C.

[0326] Synthesis Example 16

[0327] [ka]

[0328] Under an argon atmosphere, 2-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-3-yl}-4,6-bis[(1,1'-biphenyl)-4-yl]-1,3,5-triazine (4.20g, 6.33mmol), 5-chloro-2-(naphthylene-1-yl)pyridine (1.82g, 7.60mmol), palladium acetate (0.03g, 0.13mmol) and X-Phos (0.12g, 0.25mmol) were dissolved in tetrahydrofuran (70mL). To this was added 2M tripotassium phosphate aqueous solution (9.5mL, 18.9mmol) and stirred at 65℃ for 24 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). The solid was suspended in ethyl acetate (50 mL), stirred at 75° C., and then allowed to cool. The precipitated solid was filtered off, suspended in toluene (1000 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered off and washed with toluene (5 mL) and ethanol (10 mL) to obtain the desired white solid of 4,6-bis[(1,1'-biphenyl)-4-yl]-2-{3'-[2-(naphthylene-1-yl)pyridin-4-yl][1,1'-biphenyl]-3-yl}-1,3,5-triazine (compound I273-2) (yield 2.8 g, 59%).

[0329] 1 H-NMR (CDCl 3 )δ(ppm):9.12-9.11(m,1H),9.11(t,J=1.7Hz,1H),8.93-8.87(m,5H),8.25-8.22(m,1H),8.18(dd,J=8.1,2.3Hz,1H),8.06(t,J=2.0Hz,1H),7. 98-7.95(m,3H),7.89-7.85(m,5H),7.80-7.71(m,9H),7.62(dd,J=8.3, 7.0Hz, 1H), 7.54 (d, J=2.6Hz, 2H), 7.53-7.51 (m, 4H), 7.47-7.42 (m, 2H).

[0330] Synthesis Example 17

[0331] [ka]

[0332] Under an argon atmosphere, 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-3-yl}-1,3,5-triazine (3.00g, 5.11mmol), 5-chloro-2-(naphthylene-1-yl)pyridine (1.47g, 6.13mmol), palladium acetate (0.023g, 0.10mmol) and X-Phos (0.097g, 0.20mmol) were dissolved in tetrahydrofuran (51mL). To this was added 2M tripotassium phosphate aqueous solution (7.7mL, 15.3mmol) and stirred at 65°C for 23 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). The solid was suspended in toluene (300 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (15 mL) to obtain the desired white solid of 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-[2-(naphthylene-1-yl)pyridin-4-yl][1,1'-biphenyl]-3-yl}-1,3,5-triazine (compound I272-2) (yield: 1.7 g, 53%).

[0333] 1 H-NMR (CDCl 3 )δ(ppm):9.12-9.11(m,1H),9.11(t,J=1.8Hz,1H),8.91-8.84(m,5H),8.25-8.22(m,1H),8.17(dd,J=8.7,2.8Hz,1H),8.06(t,J =1.8Hz,1H),7.98-7.94(m,3H),7.87-7.84(m,3H),7.80-7.71(m,7H),7.66-7.60(m,4H),7.55-7.50(m,4H),7.47-7.42(m,1H).

[0334] Synthesis Example 7

[0335] [ka]

[0336] Under an argon stream, 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}-1,3,5-triazine (3.00g, 5.87mmol), 2-bromo-6-chloropyridine (1.35g, 7.04mmol), and tetrakis(triphenylphosphine)palladium(0) (136mg, 0.12mmol) were suspended in tetrahydrofuran (59mL). A 2.0M aqueous solution of potassium carbonate was added to the suspension, and the mixture was stirred at 65°C for 17 hours. After cooling to room temperature, the precipitated solid was filtered off. The solid was washed with water (50mL) and ethanol (50mL). The solid was suspended in toluene (120mL), stirred at 110°C, and then cooled. The precipitated solid was filtered off and washed with toluene (15 mL) to obtain a white solid of 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3-(2-chloropyridin-6-yl)phenyl}-1,3,5-triazine (yield: 1.9 g, 66%).

[0337] Synthesis Example 18

[0338] [ka]

[0339] Under an argon atmosphere, 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3-(2-chloropyridin-6-yl)phenyl}-1,3,5-triazine (1.9 g, 3.88 mmol) obtained in Synthesis Example-7, 5,5-dimethyl-2-phenanthrenyl-1,3,2-dioxaborinane (1.46 g, 5.05 mmol), palladium acetate (0.017 g, 0.078 mmol) and X-Phos (0.074 g, 0.16 mmol) were dissolved in tetrahydrofuran (74 mL). To this was added 2.0 M potassium carbonate aqueous solution (5.8 mL, 11.7 mmol) and stirred at 65 ° C for 23 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50 mL) and ethanol (50 mL). This solid was suspended in toluene (250 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to obtain the target white solid of 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-{[2-(phenanthren-9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I2-3) (yield: 0.9 g, 38%).

[0340] 1 H-NMR (CDCl 3 )δ(ppm):9.57(t,J=1.8Hz,1H),8.91-8.79(m,8H),8.46(d,J=7.7Hz,1H),8.40(d,J=9.2Hz,1H),8.06(t ,J=4.7Hz,3H),8.02(d,J=8.2Hz,1H),7.83(d,J=8.9Hz,2H),7.76-7.53(m,12H),7.46(t,J=6.9Hz,1H).

[0341] Synthesis Example 19

[0342] [ka]

[0343] Under an argon atmosphere, 2-{3-(trifluoromethanesulfonyloxy)phenyl}-4,6-bis([1,1'-biphenyl]-4-yl)triazine (4.00g, 6.56mmol), 2-(phenanthren-9-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (3.0g, 7.88mmol), palladium acetate (0.029g, 0.131mmol) and X-Phos (0.125g, 0.26mmol) were dissolved in tetrahydrofuran (120mL). To this was added 2.0M potassium carbonate aqueous solution (9.9mL, 11.7mmol) and stirred at 65°C for 20 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (50mL) and ethanol (50mL). This solid was suspended in toluene (1450 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to obtain the target white solid of 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{[2-(phenanthren-9-yl)pyrimidin-5-yl]-phenyl-3-yl}-1,3,5-triazine (compound I131-3) (yield: 2.4 g, 51%). FDMS:715

[0344] Synthesis Example 8

[0345] [ka]

[0346] Under an argon atmosphere, 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}-1,3,5-triazine (15.0g, 25.5mmol), 2-bromo-6-chloropyridine (14.7g, 76.6mmol), and tetrakis(triphenylphosphine)palladium(0) (885mg, 0.77mmol) were suspended in tetrahydrofuran (260mL). 4M aqueous potassium phosphate solution (19.2mL, 76.6mmol) was added to the suspension, and the mixture was stirred at 65°C for 17 hours. After cooling to room temperature, the precipitated solid was filtered off. The solid obtained was washed with water (50mL) and ethanol (150mL). This solid was suspended in toluene (140 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (15 mL) to obtain a white solid of 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{3-(2-chloropyridin-6-yl)phenyl}-1,3,5-triazine (yield: 12.1 g, 83%).

[0347] Synthesis Example 20

[0348] [ka]

[0349] Under an argon atmosphere, 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropyridin-6-yl)phenyl}-1,3,5-triazine (12.0 g, 20.9 mmol) obtained in Synthesis Example-8, 5,5-dimethyl-2-phenanthrenyl-1,3,2-dioxaborinane (7.90 g, 27.2 mmol), palladium acetate (0.094 g, 0.42 mmol) and X-Phos (0.399 g, 0.84 mmol) were dissolved in tetrahydrofuran (250 mL). 4M aqueous potassium phosphate solution (15.7 mL, 62.8 mmol) was added to the mixture and stirred at 65°C for 6 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (150 mL) and ethanol (10 mL). This solid was suspended in toluene (800 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to obtain the target white solid of 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{[2-(phenanthren-9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-3) (yield: 9.9 g, 66%).

[0350] FDMS:714 The glass transition temperature of compound I3-3 was 120°C.

[0351] Synthesis Example 21

[0352] [ka]

[0353] Under an argon atmosphere, 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropyridin-6-yl)phenyl}-1,3,5-triazine (3.0 g, 5.24 mmol) obtained in Synthesis Example-8, dibenzofuran-4-boronic acid (1.22 g, 5.77 mmol), palladium acetate (0.024 g, 0.10 mmol) and X-Phos (0.100 g, 0.210 mmol) were dissolved in tetrahydrofuran (50 mL). 4 M aqueous potassium phosphate solution (3.93 mL, 15.7 mmol) was added to the mixture and stirred at 65°C for 12 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (150 mL) and ethanol (10 mL). This solid was suspended in toluene (600 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (15 mL) to obtain the target white solid of 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{[2-(dibenzofuran-4-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-5) (yield: 2.4 g, 65%). FDMS:705

[0354] Synthesis Example 22

[0355] [ka]

[0356] Under an argon atmosphere, 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{3-(2-chloropyridin-6-yl)phenyl}-1,3,5-triazine (3.0 g, 5.24 mmol) obtained in Synthesis Example-8, dibenzophene-4-boronic acid (1.55 g, 6.82 mmol), palladium acetate (0.024 g, 0.10 mmol) and X-Phos (0.100 g, 0.210 mmol) were dissolved in tetrahydrofuran (50 mL). 4 M aqueous potassium phosphate solution (3.93 mL, 15.7 mmol) was added to the mixture and stirred at 65°C for 20 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (150 mL) and ethanol (10 mL). This solid was suspended in toluene (900 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered off and washed with toluene (15 mL) to obtain the target white solid of 2,4-bis[(1,1′-biphenyl)-4-yl]-6-{[2-(dibenzothiophen-4-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (Compound I3-5) (yield: 2.5 g, 66%). FDMS:721

[0357] Synthesis Example 23

[0358] [ka]

[0359] Under an argon stream, 2,4-di-(naphthyl-2-yl)-6-{3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}-1,3,5-triazine (2.50 g, 4.67 mmol), 3-chloro-2-(anthracen-9-yl)pyridine (1.49 g, 5.13 mmol), palladium acetate (0.021 g, 0.093 mmol) and X-Phos (0.089 g, 0.187 mmol) were dissolved in tetrahydrofuran (47 mL). 4 M aqueous potassium phosphate solution (3.50 mL, 14.0 mmol) was added and stirred at 65 ° C for 18 hours. After cooling to room temperature, the precipitated solid was filtered off. The obtained solid was washed with water (100 mL) and ethanol (10 mL). This solid was suspended in toluene (400 mL), stirred at 110° C., and then allowed to cool. The precipitated solid was filtered and washed with toluene (15 mL) to obtain the target white solid of 2-{[2-(anthracen-9-yl)pyridin-3-yl]phenyl-3-yl}-4,6-di-(naphthyl-2-yl)-1,3,5-triazine (compound I85-4) (yield: 1.2 g, 39%). FDMS:663

[0360] [Table 5]

[0361] Compared with ETL-3 and ETL-4 (see below) described in Patent Document 2, the cyclic azine compound according to one embodiment of the present invention has a high crystallization temperature or no crystallization peak is detected, indicating that it is difficult to crystallize and has high amorphousness.

[0362] [ka]

[0363] Next, the obtained compound was used to carry out element evaluation.

[0364] Element Example 1 (see Figure 2) (Preparation of substrate 101 and anode 102) A glass substrate with an indium-tin oxide (ITO) transparent electrode, on which a 2 mm wide ITO film (thickness: 110 nm) was patterned in stripes, was prepared as a substrate with an anode on its surface. The substrate was then washed with isopropyl alcohol and then subjected to surface treatment with ozone ultraviolet cleaning.

[0365] (Preparation for vacuum deposition) After cleaning and surface treatment, each layer was deposited by vacuum deposition on the substrate by vacuum deposition, so that each layer was laminated. First, the glass substrate was placed in a vacuum deposition chamber and 1.0×10 -4 The pressure was reduced to 10 Pa. Then, each layer was formed according to the film formation conditions in the following order.

[0366] (Fabrication of Hole Injection Layer 103) Sublimation purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were deposited at a rate of 0.15 nm / sec to form a 10 nm film, forming a hole injection layer 103.

[0367] (Preparation of the first hole transport layer 1051) Sublimation purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was formed into a film of 85 nm at a rate of 0.15 nm / sec to prepare a first hole transport layer 1051 .

[0368] (Preparation of second hole transport layer 1052) Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1′-biphenyl-4-yl)amine was formed into a film of 5 m at a rate of 0.15 nm / sec to prepare a second hole transport layer 1052 .

[0369] (Fabrication of the Light-Emitting Layer 106) Sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene were mixed in a ratio of 95:5 (mass ratio) to form a 20 nm film, producing the light-emitting layer 106. The film formation rate was 0.18 nm / sec.

[0370] (Preparation of First Electron Transport Layer 1071) Sublimation-purified 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine was formed into a film of 6 nm at a speed of 0.05 nm / sec to prepare a first electron transport layer 1071 .

[0371] (Preparation of second electron transport layer 1072) The 4,6-diphenyl-2-(3'-{4-phenyl-6-[(1,1'-biphenyl)-4-yl]pyridin-2-yl}-biphenyl-4-yl)-1,3,5-triazine (compound B1-50) synthesized in Synthesis Example-1 and Liq were formed into a film of 25 nm in a ratio of 50:50 (mass ratio) to prepare a second electron transport layer 1072. The film formation speed was 0.15 nm / sec.

[0372] (Preparation of cathode 108) Finally, a metal mask was placed perpendicular to the ITO stripes on the substrate, and the cathode 108 was formed. The cathode had a two-layer structure, with silver / magnesium (mass ratio 1 / 10) and silver being formed in that order to thicknesses of 80 nm and 20 nm, respectively. The silver / magnesium film formation rate was 0.5 nm / sec, and the silver film formation rate was 0.2 nm / sec.

[0373] As a result, the light-emitting area of ​​4 mm2 shown in Figure 2 2 An organic electroluminescence device 100 was produced. The film thickness of each layer was measured using a stylus film thickness measuring instrument (DEKTAK, manufactured by Bruker).

[0374] Furthermore, this element was sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations of 1 ppm or less by sealing a glass sealing cap and the film-formed substrate (element) with bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation).

[0375] A direct current was applied to the organic electroluminescent device fabricated as described above, and the light-emitting characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse). 2 The current efficiency (cd / A) was measured when current was passed through the device, and the device life (h) during continuous lighting was measured. The device life (h) in Table 3 was measured when the device was fabricated with an initial luminance of 1000 cd / m 2 The luminance decay time was measured when the device was continuously lit when driven at 1000 Hz, and the luminance (cd / m 2 The time required for the capacitance to decrease by 5% was measured. The driving voltage, current efficiency, and element life are relative values ​​with the result of Reference Example 1 of the element described later taken as the reference value (100). The measurement results are shown in Table 3.

[0376] Element Example 2 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example-1, except that 2-(3'-{4-phenyl-6-[4-(3-pyridyl)phenyl]pyridyl-2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (compound B1-75) synthesized in Synthesis Example-2 was used instead of compound B1-50 in Element Example-1. The measurement results obtained are shown in Table 6.

[0377] Element Example 3 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example 1, except that 2-{3'-[2-(1-naphthyl)-6-phenylpyridyl-4-yl]-1,1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (C1-57) synthesized in Synthesis Example 3 was used instead of compound B1-50 in Element Example 1. The measurement results obtained are shown in Table 6.

[0378] Element Example 4 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example 1, except that 2-{3'-[4-(1-naphthyl)-6-phenylpyridyl-2-yl]-1,1'-biphenyl-4-yl}-4,6-diphenyl-1,3,5-triazine (A1-57) synthesized in Synthesis Example 4 was used instead of Compound B1-50 in Element Example 1. The measurement results obtained are shown in Table 6.

[0379] Element Example 5 In the element example 1, except that 2-(3'-{6-phenyl-2-[(1,1'-biphenyl)-4-yl]pyridin-2-yl}-1,1'-biphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (C1-50) synthesized in synthesis example 5 was used instead of compound B1-50, an organic electroluminescence device was prepared and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 6.

[0380] Element Example 6 An organic electroluminescent device was produced and evaluated in the same manner as in Element Example-1, except that 2-(3'-(2,6-diphenylpyridin-4-yl}-1,1'-biphenyl-4-yl)-4-(1,1'-biphenyl)-6-phenyl-1,3,5-triazine (C2-1) synthesized in Synthesis Example-6 was used instead of compound B1-50 in Element Example-1. The measurement results obtained are shown in Table 6.

[0381] Element Example 7 An organic electroluminescent device was produced and evaluated in the same manner as in Element Example-1, except that 2-(3'-(4,6-diphenylpyridin-2-yl}-1,1'-biphenyl-4-yl)-4-(1,1'-biphenyl)-6-phenyl-1,3,5-triazine (A2-1) synthesized in Synthesis Example-7 was used instead of compound B1-50 in Element Example-1. The measurement results obtained are shown in Table 6.

[0382] Element Example 8 An organic electroluminescent device was produced and evaluated in the same manner as in Element Example-1, except that 2-[(3″-(2,6-diphenylpyridin-4-yl)-1,1′:3′:1″-terphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (F13-1) synthesized in Synthesis Example-8 was used instead of compound B1-50 in Element Example-1. The measurement results obtained are shown in Table 6. Element Example 9 An organic electroluminescent device was prepared and evaluated in the same manner as in Element Example-1, except that 2-[(3'''-(2,6-diphenylpyridin-4-yl)-1,1':4',1'':3'',1'''-quaterphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine (G3-1) synthesized in Synthesis Example-9 was used instead of compound B1-50 in Element Example-1. The measurement results obtained are shown in Table 6. Element reference example 1 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example 1, except that 2-[5-(9-phenanthryl)-4'-(2-pyrimidyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (ETL-2) described in JP2011-063584A was used instead of compound B1-50 in Element Example 1. The measurement results obtained are shown in Table 6.

[0383] [Table 6]

[0384] Device Example 10 In the element example 1, except that 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-6-yl}-1,1'-biphenyl-4-yl]-1,3,5-triazine (compound I171-3) synthesized in synthesis example 10 was used instead of compound B1-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0385] Element Example 11 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example-1, except that 4,6-diphenyl-2-[3'-{2-(9-phenanthryl)pyridin-4-yl}1,1'-biphenyl-4-yl]-1,3,5-triazine (compound I179-3) synthesized in Synthesis Example-11 was used instead of compound B-50 in Element Example-1. The measurement results obtained are shown in Table 7.

[0386] Element Example 12 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example-1, except that 4,6-diphenyl-2-[3'-{5-(9-phenanthrenyl)pyridin-3-yl}-1,1'-biphenyl-4-yl]-1,3,5-triazine (compound I187-3) synthesized in Synthesis Example-12 was used instead of compound B-50 in Element Example-1. The measurement results obtained are shown in Table 7.

[0387] Element Example 13 In the element example 1, except that 4,6-bis[(1,1'-biphenyl)-4-yl]-2-[{5-(phenanthren-9-yl)pyridin-3-yl}-phenyl-3-yl)}-1,3,5-triazine (compound I127-3) synthesized in synthesis example 13 was used instead of compound B-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0388] Element Example 14 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example 1, except that 2,4-diphenyl-6-[3-(3-methyl-2-phenanthrenylpyridin-4-yl)phenyl]-1,3,5-triazine (compound I141-3) synthesized in Synthesis Example 14 was used instead of compound B-50 in Element Example 1. The measurement results obtained are shown in Table 7.

[0389] Element Example 15 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example-1, except that 2,4-diphenyl-6-[3-(2-methyl-3-phenanthrenylpyridin-6-yl)phenyl]-1,3,5-triazine (compound I153-3) synthesized in Synthesis Example-15 was used instead of compound B-50 in Element Example-1. The measurement results obtained are shown in Table 7.

[0390] Element Example 16 In the element example 1, except that 4,6-bis[(1,1'-biphenyl)-4-yl]-2-{3'-[2-(naphthylene-1-yl)pyridin-4-yl][1,1'-biphenyl]-3-yl}-1,3,5-triazine (compound I273-2) synthesized in synthesis example 16 was used instead of compound B-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0391] Element Example 17 In the element example 1, except that 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{3'-[2-(naphthylene-1-yl)pyridin-4-yl][1,1'-biphenyl]-3-yl}-1,3,5-triazine (compound I272-2) synthesized in synthesis example 17 was used instead of compound B-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0392] Element Example 18 In the element example 1, except that 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-{[2-(phenanthren-9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (compound I2-3) synthesized in synthesis example 18 was used instead of compound B-50, an organic electroluminescence device was prepared and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0393] Element Example 19 In the element example 1, except that 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{[2-(phenanthren-9-yl)pyrimidin-5-yl]-phenyl-3-yl}-1,3,5-triazine (compound I131-3) synthesized in synthesis example 19 was used instead of compound B-50, an organic electroluminescence device was prepared and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0394] Element Example 20 In the element example 1, except that 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{[2-(phenanthren-9-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (compound I3-3) synthesized in synthesis example 20 was used instead of compound B-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0395] Element Example 21 In the element example 1, except that 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{[2-(dibenzofuran-4-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (compound I3-5) synthesized in synthesis example 21 was used instead of compound B-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0396] Element Example 22 In the element example 1, except that 2,4-bis[(1,1'-biphenyl)-4-yl]-6-{[2-(dibenzothiophen-4-yl)pyridin-6-yl]phenyl-3-yl}-1,3,5-triazine (compound I3-6) synthesized in synthesis example 22 was used instead of compound B-50, an organic electroluminescence device was produced and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0397] Element Example 23 In the element example 1, except that 2-{[2-(anthracen-9-yl)pyridin-3-yl]phenyl-3-yl}-4,6-di-(naphthyl-2-yl)-1,3,5-triazine (compound I85-4) synthesized in synthesis example 23 was used instead of compound B-50, an organic electroluminescence device was prepared and evaluated in the same manner as in element example 1. The measurement results obtained are shown in Table 7.

[0398] Element reference example 2 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example 1, except that 2,4-bis[(1,1'-biphenyl)-4-yl]-6-[4'-(3-pyridyl)1,1'-biphenyl-4-yl]-1,3,5-triazine (ETL-3) described in Patent Document 2 was used instead of Compound B-50 in Element Example 1. The measurement results obtained are shown in Table 2.

[0399] Element reference example 3 An organic electroluminescence device was produced and evaluated in the same manner as in Element Example 1, except that 2,4-bis[(1,1'-biphenyl)-4-yl]-6-[4'-(4-pyridyl)1,1'-biphenyl-4-yl]-1,3,5-triazine (ETL-4) described in Patent Document 2 was used instead of Compound B-50 in Element Example 1. The measurement results obtained are shown in Table 2.

[0400] [Table 7]

[0401] The cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention have extremely excellent heat resistance of the film quality, and by using the compounds, it is possible to provide an organic electroluminescence device having a long life and excellent current efficiency. The cyclic azine compounds (1), (11), and (21) according to an embodiment of the present invention are used as electron transport materials for organic electroluminescence devices that are excellent in low driving voltage. Furthermore, the cyclic azine compounds (1), (11), and (21) can provide organic electroluminescence devices with low power consumption. In addition, the cyclic azine compound according to one embodiment of the present invention has good thermal stability during sublimation purification, and therefore has excellent operability during sublimation purification, and can provide a material with less impurities that cause deterioration of organic electroluminescence elements.In addition, the cyclic azine compound according to one embodiment of the present invention has excellent stability of a vapor deposition film, and therefore can provide an organic electroluminescence element with a long life. Furthermore, thin films comprising the cyclic azine compounds (1), (11), and (21) according to an embodiment of the present invention are excellent in electron transporting ability, hole blocking ability, oxidation-reduction resistance, water resistance, oxygen resistance, electron injection properties, etc., and are therefore useful as materials for organic electroluminescent elements, and are useful as electron transporting materials, hole blocking materials, light-emitting host materials, etc. They are particularly useful when used as electron transporting materials. Furthermore, the cyclic azine compounds (1), (11), and (21) according to one embodiment of the present invention have a wide band gap and a high triplet excitation level, and therefore can be suitably used not only in conventional fluorescent device applications but also in phosphorescent devices and organic electroluminescent devices utilizing thermally activated delayed fluorescence (TADF). [Explanation of symbols]

[0402] 1,101 PCBs 2,102 Anode 3,103 Hole injection layer 4. Charge generation layer 5,105 Hole transport layer 6,106 emitting layer 7,107 Electron transport layer 8,108 Cathode 51,1051 First hole transport layer 52,1052 Second hole transport layer 71,1071 First electron transport layer 72,1072 Second electron transport layer 100 Organic electroluminescent device

Claims

1. A cyclic azine compound represented by formula (11): 【Chemistry 1】 In formula (11), Ar １１ , and Ar １２ each independently represents a phenyl group or a naphthyl group; Ar １３ , and Ar １４ are each independently a monocyclic ring which may be linked, a condensed ring which may be linked, or a structure in which these are linked; (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, (ii) a nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and consisting only of 6-membered rings, or (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) a group formed by combining any two or more selected from (i) to (iii) above; Ar １３ , and Ar １４ The total number of ring carbon atoms is 4 to 25; Ar １３ , and Ar １４ At least one of (i) an aromatic hydrocarbon group having 6 to 24 carbon atoms, (iii) a heteroaromatic group having 4 to 25 carbon atoms and composed of atoms selected from the group consisting of H, C, O, and S, or (iv) a group formed by combining any two or more selected from (i) and (iii); L １１ represents a phenylene group or a single bond; Z １１ and Z １２ one of them represents a nitrogen atom and the other represents C—H; n １１ is 1 or 2. Ar １１ ~Ar １４ Each group represented by the formula (I) may independently have one or more groups selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

2. Ar １１ , and Ar １２ are each independently a phenyl group or a naphthyl group; Ar １１ , and Ar １２ 2. The cyclic azine compound according to claim 1, wherein when each group represented by: is a phenyl group, the phenyl groups each independently may have a phenyl group.

3. Ar １３ , and Ar １４ The cyclic azine compound according to claim 1 or 2, wherein none of the following has a substituent:

4. Ar １３ , and Ar １４ The cyclic azine compound according to any one of claims 1 to 3, wherein the total number of ring-constituting carbon atoms of each of the above formulas is 4 to 20.

5. Ar １３ The total number of ring carbon atoms of Ar １４ 5. The cyclic azine compound according to claim 1, wherein the sum of the total number of ring-constituting carbon atoms of and is 11 to 32.

6. Ar １３ , and Ar １４ each independently represents a phenyl group, a p-tolyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3-(2-pyridyl)phenyl group, a 4-(2-pyridyl)phenyl group, a 3-(3-pyridyl)phenyl group, a 4-(3-pyridyl)phenyl group, a 3-(4-pyridyl)phenyl group, a 4-(4-pyridyl)phenyl group, a 2-(1-naphthyl)phenyl group, a 3-(1-naphthyl)phenyl group, a 2-(2-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 2-(9-anthryl)phenyl group, 3-(9-anthryl)phenyl group, 3-(3-fluoranthenyl)phenyl group, 4-(3-fluoranthenyl)phenyl group, 3-(2-triphenylenyl)phenyl group, 4-(2-triphenylenyl)phenyl group, 3-(3-quinolyl)phenyl group, 4 -(3-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 3-(8-quinolyl)phenyl group, 4-(8-quinolyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 3-(2-dibenzofuryl)phenyl group, 4-(2-dibenzothienyl)phenyl group 6. The cyclic azine compound according to claim 1, wherein the aryl group is a phenyl group, a 3-(4-dibenzofuryl)phenyl group, a 4-(4-dibenzofuryl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 3-quinolyl group, an 8-quinolyl group, a 2-benzothienyl group, a 2-benzofuryl group, a 9-anthryl group, a 9-phenanthryl group, a 2-dibenzothienyl group, a 2-dibenzofuryl group, a 4-dibenzothienyl group, or a 4-dibenzofuryl group.

7. n １１ The cyclic azine compound according to any one of claims 1 to 6, wherein

8. L １１ The cyclic azine compound according to any one of claims 1 to 7, wherein is a single bond.

9. A material for an organic electroluminescent device, comprising the cyclic azine compound according to any one of claims 1 to 8.

10. An organic electroluminescent device comprising the cyclic azine compound according to any one of claims 1 to 8.

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