KR102424486B1 - Triazine compound, manufacturing method thereof, and organic electroluminescent device comprising the same - Google Patents

Abstract

(일반식 (1) 중, Ar¹은 페닐기를 나타내고, 2개의 Ar¹은 동일하다. Ar², Ar³, Ar⁵ 및 Ar⁶은, 각각 독립적으로 단일결합 등을 나타낸다. Ar⁴ 및 Ar⁷은, 각각 독립적으로, (a) 탄소수 6 내지 24의 단환 또는 축환 방향족 탄화수소기를 나타낸다. Ar², Ar³ 및 Ar⁴의 환 구성 탄소 원자의 총수 및 Ar⁵, Ar⁶ 및 Ar⁷의 환 구성 탄소 원자의 총수는 어느 쪽이나 5 내지 25이다. A는 단일결합을 나타낸다. B¹ 및 B²는 단일결합 또는 수소 원자를 나타낸다. 단, B¹ 또는 B² 중 어느 한쪽이 단일결합을 나타내고 A와 단일결합을 형성하며, 다른 한쪽은 수소 원자를 나타낸다. Z¹ 및 Z²는, 각각 독립적으로, 질소 원자 또는 C-H를 나타낸다. 단, Z¹ 또는 Z² 중 어느 한쪽이 질소 원자를 나타내고, 다른 한쪽은 C-H를 나타낸다).The present invention provides a triazine compound represented by the following general formula (1), which is excellent in heat resistance and useful as an electron transport material having excellent long-life, low-voltage driving, or luminous efficiency of an organic electroluminescent device:

(In general formula (1), Ar ¹ represents a phenyl group, and two Ar ¹ are the same. Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ each independently represent a single bond or the like. Ar ⁴ and Ar ⁷ each independently represents (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, the total number of ring-constituting carbon atoms of Ar ² , Ar ³ and Ar ⁴ and the ring-constituting carbons of Ar ⁵ , Ar ⁶ and Ar ⁷ The total number of atoms is either 5 to 25. A represents a single bond. B ¹ and B ² represents a single bond or a hydrogen atom, provided that either B ¹ or B ² represents a single bond and is single with A form a bond, and the other side represents a hydrogen atom.Z ¹ and Z ² each independently represents a nitrogen atom or CH. However, either Z ¹ or Z ² represents a nitrogen atom, and the other represents CH).

Description

Triazine compound, manufacturing method thereof, and organic electroluminescent device comprising the same

The present invention relates to a triazine compound, a method for producing the same, and an organic electroluminescent device containing the same. More specifically, it relates to a triazine compound useful as a material for an organic electroluminescent device, characterized by a structure in which a diarylpyridyl group is combined with a triazine skeleton via a meta bond or an ortho bond, and a method for producing the same, It relates to an organic electroluminescent device with high efficiency, low voltage and high durability, characterized in that a triazine compound is used in at least one layer of the organic compound layer.

The organic electroluminescent device has a basic configuration in which a light emitting layer containing a light emitting material is placed between a hole transport layer and an electron transport layer, and an anode and a cathode are attached to the outside thereof. By recombination of holes and electrons injected into the light emitting layer It is a light emitting device that utilizes light emission (fluorescence or phosphorescence) when generated excitons are deactivated, and is already used not only for small displays but also for large televisions and lighting. In addition, the hole transport layer may be divided into a hole transport layer and a hole injection layer, the light emitting layer may be divided into an electron block layer, a light emitting layer, and a hole block layer, and the electron transport layer may be divided into an electron transport layer and an electron injection layer. In addition, as a carrier transport layer (electron transport layer or hole transport layer) of the organic electroluminescent device, a co-evaporation film doped with a metal, an organometallic compound, or other organic compound may be used.

The conventional organic electroluminescent device has a high driving voltage, low light emitting luminance and luminous efficiency, and a remarkably low device lifetime, as compared with inorganic light emitting diodes, and has not been put to practical use. Although organic electroluminescent devices in recent years have been gradually improved, more excellent materials are required in terms of luminous efficiency characteristics, driving voltage characteristics, and long life characteristics. Moreover, high heat resistance may be required depending on uses, such as an in-vehicle use, and a high glass transition temperature (Tg) is calculated|required of a material.

As an electron transport material excellent in long life for organic electroluminescent devices, the triazine compound disclosed in patent document 1 is mentioned. However, further improvement has been demanded in terms of voltage, lifetime, and luminous efficiency of an organic electroluminescent device using the material.

Patent Document 2 discloses a triazine compound having a diarylpyridyl group and the like. Although the said compound is excellent in the point of high luminous efficiency of an organic electroluminescent element, further improvement of luminous efficiency has been calculated|required.

JP 2011-063584 A WO 2016002864 A

SUMMARY OF THE INVENTION It is an object of the present invention to provide an electron transporting material which is excellent in heat resistance of film quality and excellent in low voltage driveability, luminous efficiency or long life of an organic electroluminescent device.

The present inventors, as a result of repeated intensive studies in order to solve the above problems, a triazine compound in which a diarylpyridyl group and a triazine moiety are bonded via a meta bond or an ortho bond (hereinafter, "triazine compound (1)" The organic electroluminescent device using the compound as an electron transport material with high heat resistance of the film quality of (also referred to as came to completion.

That is, the present invention relates to a triazine compound represented by the following general formula (1), a method for producing the same, and an organic electroluminescent device using the same:

(in general formula (1),

Ar ¹ represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group), and two Ar ¹ are the same.

Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heterocyclic group having 3 to 25 carbon atoms consisting only of a 6-membered ring An aromatic group, (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S (the groups represented by (a), (b) and (c) are , a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond.

Ar ⁴ and Ar ⁷ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or (c) ) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of H, C, O and S (the group represented by (a), (b) and (c) is a fluorine atom, may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).

The total number of ring-constituting carbon atoms of Ar ² , Ar ³ and Ar ⁴ and the total number of ring-constituting carbon atoms of Ar ⁵ , Ar ⁶ and Ar ⁷ are 5 to 25 in either case.

A represents a single bond.

B ¹ and B ² represent a single bond or a hydrogen atom. However, either one of B ¹ or B ² represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.

Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, either Z ¹ or Z ² represents a nitrogen atom, and the other represents CH.)

That is, the present invention exists in the following [1] to [13].

[1] A triazine compound represented by the general formula (1).

[2] The triazine compound according to [1], wherein Ar ¹ represents a phenyl group, a tolyl group, a naphthyl group or a biphenyl group, and two Ar ¹ are the same.

[3] The triazine compound according to [1] or [2], wherein all of Ar ¹ are phenyl groups.

[4] Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b′) a monocyclic ring having 3 to 11 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms consisting of atoms selected from the group consisting of H, C, O and S (corresponding (a), (b') and (c) The group represented by ) is a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar ⁴ and Ar ⁷ is, each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b′) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting only of a 6-membered ring, or (c) H , C, O, and S monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of S (the groups represented by (a), (b') and (c) are a fluorine atom, carbon number The triazine compound according to [1], [2] or [3], characterized in that it is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).

[5] Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluorine group Lantenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (These groups may have a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar ⁴ and Ar ⁷ is, each independently, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluoranthenyl group, a triphenylenyl group, a triazyl group, A pyrimidyl group, a piperazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group (these groups are fluorine atoms, having 1 to 4 carbon atoms) The triazine compound according to [1], [2], [3], [4] or [5], characterized in that it is an alkyl group or an alkoxy group having 1 to 4 carbon atoms).

[6] Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluorine group Lantenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (These groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar ⁴ and Ar ⁷ are each independently a phenyl group, a naphthyl group, Fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, peryleneyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, qui Nolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group or dibenzothienyl group (these groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms) ), the triazine compound according to [1], [2], [3], [4] or [5].

[7] A group represented by -Ar ² -Ar ³ -Ar ⁴ and a group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, fluoran tenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, Pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or In [1], [2], [3], [4], [5] or [6], characterized in that it is a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group). A described triazine compound.

[8] A group represented by -Ar ² -Ar ³ -Ar ⁴ and a group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridyl group Phenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group , which is a naphthyl group, a phenanthryl group, a dibenzothienyl group or a dibenzofuryl group (these groups may be substituted with a methyl group), [1], [2], [3], [4], [5], The triazine compound according to [6] or [7].

[9] Either one of the group represented by -Ar ² -Ar ³ -Ar ⁴ or the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridylphenyl group , pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and the other is a phenyl group, a biphenyl group, a pyridyl group, or a naphthyl group (these groups may be substituted with a fluorine atom or a methyl group). The triazine compound according to [1], [2], [3], [4], [5], [6], [7] or [8], wherein the group may be substituted with a methyl group.

[10] Either one of the group represented by -Ar ² -Ar ³ -Ar ⁴ or the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridylphenyl group , pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group or a dibenzofuryl group (these groups may be substituted with a methyl group), and the other is a phenyl group or a naphthyl group, [1], [2], [3], The triazine compound according to [4], [5], [6], [7], [8] or [9].

[11] The method for producing a triazine compound according to [1], wherein a coupling reaction is used.

[12] A material for an organic electroluminescent device comprising the triazine compound according to [1].

[13] An electron transporting material for an organic electroluminescent device comprising the triazine compound according to [1].

According to the present invention, it is possible to provide a triazine compound having excellent film quality and heat resistance, and to provide an organic electroluminescent device excellent in low voltage, luminous efficiency or long lifespan.

Hereinafter, the present invention will be described in detail.

The present invention relates to the triazine compound (1), a method for producing the same, and to providing a material for an organic electroluminescent device using the material.

The substituents in the triazine compound (1) of the present invention are respectively defined as follows.

In formula (1), Ar ¹ represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group), and two Ar ¹ are the same.

In Ar ¹ , the phenyl group or naphthyl group substituted with a fluorine atom is not particularly limited, but a fluorophenyl group, a pentafluorophenyl group, a difluorophenyl group, a fluoronaphthyl group or a difluoronaphthyl group is preferable. An example can be given.

Although it does not specifically limit as a phenyl group or a naphthyl group substituted by the methyl group in Ar< ¹ >, A tolyl group, a methylnaphthyl group, a dimethylphenyl group, a dimethylnaphthyl group, etc. are mentioned as a preferable example.

Although it does not specifically limit as a phenyl group or a naphthyl group substituted by the phenyl group in Ar< ¹ >, A biphenyl group, a phenylnaphthyl group, a terphenyl group, a diphenylnaphthyl group, etc. are mentioned as a preferable example.

Ar ¹ is more preferably a phenyl group, a tolyl group, a naphthyl group or a biphenyl group from the viewpoint of excellent electron-transporting material properties, and still more preferably a phenyl group from the viewpoint of easy synthesis.

Specific examples of Ar ¹ are not particularly limited, but phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group, 2- Fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, 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 , 2',4',6'-trimethylbiphenyl-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, 2',4',6'-trimethylbiphenyl-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, 2 ',4',6'-trimethylbiphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalene- 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-phenylnaphthalene-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- A preferred example is a diyl group or a 2-methylnaphthalen-8-yl group.

Among these substituents, a phenyl group, a p-tolyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is preferable from the viewpoint of excellent electron-transporting material properties, and a phenyl group, a bi A phenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is more preferable.

Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heterocyclic group having 3 to 25 carbon atoms consisting only of a 6-membered ring An aromatic group, (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S (the groups represented by (a), (b) and (c) are , a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond.

Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ may be the same or different.

In Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ , (a) the monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms is not particularly limited, but a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, A pyrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, an acenaphthyl group, a fluorenyl group, a benzofluorenyl group, etc. are mentioned as a preferable example. Moreover, as described above, these substituents may be substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ , (b) monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms and consisting only of a 6-membered ring is not particularly limited, but a pyridyl group, a pyrazyl group, a pyridyl group A midyl group, a pyridazyl group, a triazyl group, a quinolyl group, an isoquinolyl group, a phenanthridyl group, a benzoquinolyl group, an acridinyl group, etc. are mentioned as a preferable example. Moreover, the carbazolyl group is a heteroaromatic group containing a 5-membered ring, and is not included in the C3-C25 monocyclic or condensed-cyclic nitrogen-containing heteroaromatic group which consists only of a 6-membered ring of this invention. As described above, these substituents may be substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

In Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ , (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S is particularly limited. Although not, 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. are mentioned as a preferable example. Moreover, as described above, these substituents may be substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

The alkyl group having 1 to 4 carbon atoms in Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ is not particularly limited, but a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group or t-butyl group, etc. can be mentioned as a preferred example.

The alkoxy group having 1 to 4 carbon atoms in Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ is not particularly limited, but a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group Preferred examples include a period or a t-butoxy group.

Ar ⁴ and Ar ⁷ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or (c) ) A monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of H, C, O and S (the group represented by (a), (b and (c)) is a fluorine atom, carbon number may have a 1-4 alkyl group or a C1-C4 alkoxy group).

In Ar ⁴ and Ar ⁷ , (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, (c) H, C , O and S For the constituent requirements of a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms, all of Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ have the same meaning.

From the above description, the group represented by -Ar ² -Ar ³ -Ar ⁴ and the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are not particularly limited, but a phenyl group, a biphenyl group, a terphenyl group, and a naphthylphenyl group , phenanthrylphenyl group, anthrylphenyl group, pyrenylphenyl group, triphenylphenyl group, chrysenylphenyl group, fluoranthenylphenyl group, acenaphthylphenyl group, fluorenylphenyl group, naphthylbiphenyl group, naphthyl group, phenylnaphthyl group, biphenyl Naphthyl group, phenanthryl naphthyl group, anthryl naphthyl group, phenanthryl group, phenylphenanthryl group, naphthylphenanthryl group, anthryl group, phenylanthryl group, naphthylanthryl group, pyrenyl group, phenylpyrenyl group, tri Phenylenyl group, phenyltriphenylenyl group, chrysenyl group, phenylchrysenyl group, fluorantenyl group, phenylfluorantenyl group, acenaphthyl group, phenylacenaphthyl group, fluorenyl group, phenylfluorenyl group, benzoflu Orenyl group, fluorophenyl group, pentafluorophenyl group, fluorobiphenyl group, fluoroterphenyl group, fluoronaphthylphenyl group, naphthylfluorophenyl group, fluorophenanthrylphenyl group, phenanthrylfluorophenyl group, fluoroanthrylphenyl group , anthryl fluorophenyl group, fluoropyrenylphenyl group, pyrenylfluorophenyl group, fluorotriphenylphenyl group, triphenylfluorophenyl group, fluorochrysenylphenyl group, chrysenylfluorophenyl group, fluorofluoranthenylphenyl group, Fluoranthene fluorophenyl group, fluoroacenaphthylphenyl group, acenaphthylfluorophenyl group, fluorofluorenylphenyl group, fluorenylfluorophenyl group, fluoronaphthylbiphenyl group, naphthylfluorobiphenyl group, fluoro Lonaphthyl group, fluorophenylnaphthyl group, phenylfluoronaphthyl group, fluorobiphenylnaphthyl group, biphenylfluoronaphthyl group, fluorophenanthrylnaphthyl group, phenanthrylfluoronaphthyl group, fluoroanthrylnaphthyl group , anthryl fluoronaphthyl group, fluorophenanthryl group, fluorophenylphenanthryl group, phenylfluorophenanthryl group, fluoronaphthylphenanthryl group, naphthylfluorophenanthryl group, fluoroanthryl group, Fluorophenylanthryl group, phenylfluoroanthryl group, fluoronaphthylanthryl group, naphthylfluoroanthryl group, fluoropyrenyl group, fluorophenylpyrenyl group, phenylfluoropyrenyl group, fluorotriphenyl Renyl group, fluorophenyltriphenylenyl group, phenylfluorotriphenylenyl group, fluorochrysenyl group, fluorophenylchrysenyl group, phenylfluorochrysenyl group, fluorofluorantenyl group, fluorophenylfluoro Lantenyl group, phenylfluorofluoranthenyl group, fluoroacenaphthyl group, fluorophenylacenaphthyl group, phenylfluoroacenaphthyl group, fluorofluorenyl group, fluorophenylfluorenyl group, phenylfluorofluorene group Diary, fluorobenzofluorenyl group, pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazyl group, quinolyl group, isoquinolyl group, phenantridyl group, benzoquinolyl group, acridinyl group, Pyridylphenyl group, pyrazylphenyl group, pyrimidylphenyl group, pyridazylphenyl group, triazylphenyl group, quinolylphenyl group, isoquinolylphenyl group, phenantridylphenyl group, benzoquinolylphenyl group, acridinylphenyl group, (phenylpyridyl)phenyl group , (naphthylpyridyl)phenyl group, pyridylbiphenyl group, pyrazylbiphenyl group, pyrimidylbiphenyl group, pyridazylbiphenyl group, triazylbiphenyl group, quinolylbiphenyl group, isoquinolylbiphenyl group, phenantridylbiphenyl group , benzoquinolylbiphenyl group, acridinylbiphenyl group, pyridylterphenyl group, pyrazylterphenyl group, pyrimidylterphenyl group, pyridylterphenyl group, triazylterphenyl group, pyridylnaphthyl group, pyrazylnaphthyl group, pyrimidylnaphthyl group , pyridazyl naphthyl group, triazyl naphthyl group, quinolyl naphthyl group, isoquinolyl naphthyl group, phenanthridyl naphthyl group, benzoquinolyl naphthyl group, acridinyl naphthyl group, phenylpyridyl group, biphenylpyridyl group, naph Tylpyridyl group, phenanthrylpyridyl group, anthrylpyridyl group, pyrenylpyridyl group, triphenylenylpyridyl group, chrysenylpyridyl group, fluoranthenylpyridyl group, acenaphthylpyridyl group, fluorenylpyridyl group, thienyl group , furyl group, bithienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzofuryl group, thienylphenyl group, furylphenyl group, bithienylphenyl group, bifurylphenyl group, benzothienylphenyl group , benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, thienylbiphenyl group, furylbiphenyl group, benzothienylbiphenyl group, benzofurylbiphenyl group, dibenzothienylbiphenyl group, dibenzofurylbiphenyl group, thien Ilnaphthyl group, furylnaphthyl group, Benzothienylnaphthyl group, benzofurylnaphthyl group, dibenzothienylnaphthyl group, dibenzofurylnaphthyl group, phenylthienyl group, phenylfuryl group, biphenylthienyl group, biphenylfuryl group, naphthylthienyl group, naphthylfuryl group , phenanthrylthienyl group, phenanthrylfuryl group, anthrylthienyl group, anthrylfuryl group, pyrenylthienyl group, pyrenylfuryl group, triphenylenylthienyl group, triphenylenylfuryl group, chrysenylthienyl group, chrysenylfuryl group Preferable examples include a reyl group, a fluoranthenylthienyl group, a fluorantenylfuryl group, an acenaphthylthienyl group, an acenaphthylfuryl group, a fluorenylthienyl group, or a fluorenylfuryl group.

In addition, Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b′) a 6-membered ring, in view of excellent electron-transporting material properties. A monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of ), (b') and (c) may have a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms); or a single bond, and further, for Ar ⁴ and Ar ⁷ , each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b′) a monocyclic ring having 3 to 11 carbon atoms consisting only of a 6-membered ring Or a condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S (corresponding (a), (b') and The group represented by (c) is preferably a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).

In the description of the preferred range, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (c) a monocyclic ring having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S, or About a condensed ring heteroaromatic group, a C1-C4 alkyl group, and a C1-C4 alkoxy group, it is synonymous with what was mentioned above.

Although it does not specifically limit about the C3-C11 monocyclic or condensed-ring nitrogen-containing heteroaromatic group consisting only of a 6-membered ring (b') in the description of the said preferable range, A pyridyl group, a pyrazyl group, a pyrimidyl group, A pyridyl group , a triazyl group, a quinolyl group, or an isoquinolyl group are preferable examples. Moreover, a carbazolyl group is a C12 heteroaromatic group, and is not contained in the C3-C11 monocyclic or condensed-ring nitrogen-containing heteroaromatic group which consists only of a 6-membered ring of this invention. As described above, these substituents may be substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, and a pyrene in view of excellent electron transporting material properties. Diary, peryleneyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group benzofuranyl group, benzothienyl group, dibenzofuran a diyl or dibenzothienyl group (these groups may have a phenyl group, tolyl group, pyridyl group, methylpyridyl group, fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond More preferably, Ar ⁴ and Ar ⁷ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluoranthenyl group , triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group or dibenzothienyl group (these groups are , which may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).

In addition, Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, and a pyrene from the viewpoint of easy synthesis. Diary, peryleneyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group benzofuranyl group, benzothienyl group, dibenzofuran It is more preferably a diyl or dibenzothienyl group (these groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and further, for Ar ⁴ and Ar ⁷ , each independently, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluorantenyl group, a triphenylenyl group, a triazyl group, pyrimi A diyl group, a piperazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group (these groups are a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or It is preferable that it is a C1-C4 alkoxy group.).

Further, the group represented by -Ar ² -Ar ³ -Ar ⁴ and the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are each independently a phenyl group, a biphenyl group, a naph in view of excellent electron-transporting material properties. Tylphenyl group, phenanthrylphenyl group, fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group , pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, It is more preferable that they are an anthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenane Trilphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl group More preferably, they are a phenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a methyl group).

In addition, the group represented by -Ar ² -Ar ³ -Ar ⁴ and the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are easy to synthesize and have high heat resistance of the film, so -Ar ² -Ar ³ Either the group represented by -Ar ⁴ or the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ is a phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienyl Phenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzo a thienyl group or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and the other is a phenyl group, a biphenyl group, a pyridyl group or a naphthyl group (these groups may be substituted with a methyl group) more preferably, any one of the group represented by -Ar ² -Ar ³ -Ar ⁴ or the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyri Dylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyri A diyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a methyl group), and the other one is more preferably a phenyl group or a naphthyl group.

Specific examples of the group represented by -Ar ² -Ar ³ -Ar ⁴ and the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are not particularly limited, but include, for example, a 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, 3,5-di-tert-butylphenyl group, bi Phenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4- Diyl, 2,2'-dimethylbiphenyl-4-yl group, 2',4',6'-trimethylbiphenyl-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, 2',4',6'-tri Methylbiphenyl-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, 2',4',6'-trimethylbiphenyl-2-yl group, 3-ethylbiphenyl-4-yl group, 4'-ethylbiphenyl-4 -yl group, 2',4',6'-triethylbiphenyl-4-yl group, 6-ethylbiphenyl-3-yl group, 4'-ethylbiphenyl-3-yl group, 5-ethylbiphenyl-2- Diyl, 4'-ethylbiphenyl-2-yl group, 2',4',6'-triethylbiphenyl-2-yl group, 3-propylbiphenyl-4-yl group, 4'-propylbiphenyl-4- Diary, 2',4',6'-tripropylbiphenyl- 4-yl group, 6-propylbiphenyl-3-yl group, 4'-propylbiphenyl-3-yl group, 5-propylbiphenyl-2-yl group, 4'-propylbiphenyl-2-yl group, 2',4 ',6'-tripropylbiphenyl-2-yl group, 3-isopropylbiphenyl-4-yl group, 4'-isopropylbiphenyl-4-yl group, 2',4',6'-triisopropylbi Phenyl-4-yl group, 6-isopropylbiphenyl-3-yl group, 4'-isopropylbiphenyl-3-yl group, 5-isopropylbiphenyl-2-yl group, 4'-isopropylbiphenyl-2- Diyl, 2',4',6'-triisopropylbiphenyl-2-yl group, 3-butylbiphenyl-4-yl group, 4'-butylbiphenyl-4-yl group, 2',4',6' -Tributylbiphenyl-4-yl group, 6-butylbiphenyl-3-yl group, 4'-butylbiphenyl-3-yl group, 5-butylbiphenyl-2-yl group, 4'-butylbiphenyl-2- Diyl, 2',4',6'-tributylbiphenyl-2-yl group, 3-tert-butylbiphenyl-4-yl group, 4'-tert-butylbiphenyl-4-yl group, 2',4' , 6'-tritert-butylbiphenyl-4-yl group, 6-tert-butylbiphenyl-3-yl group, 4'-tert-butylbiphenyl-3-yl group, 5-tert-butylbiphenyl-2- Diyl, 4'-tert-butylbiphenyl-2-yl group, 2',4',6'-tritert-butylbiphenyl-2-yl group, 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- Diyl, 2,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-2-yl group, 3,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-5-yl group, 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, 4-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(3-methyl-2-pyri dil)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, 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-pyri dil)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-(2,4-dimethyl-3-pyridyl)phenyl group, 3-(2,4-dimethyl-3-pyridyl)phenyl group, 4-(2,4 -Dimethyl-3-pyridyl)phenyl group, 2-(3,5-dimethyl-4-pyridyl)phenyl group, 3-(3,5-dimethyl-4-pyridyl)phenyl group, 4-(3, 5-dimethyl-4-pyridyl)phenyl group, 2-(3-phenyl-2-pyridyl)phenyl group, 3-(3-phenyl-2-pyridyl)phenyl group, 4-(3-phenyl-2-pyri dil)phenyl group, 2-(4-phenyl-2-pyridyl)phenyl group, 3-(4-phenyl-2-pyridyl)phenyl group, 4-(4-phenyl-2-pyridyl)phenyl group, 2-(5 -Phenyl-2-pyridyl)phenyl group, 3-(5-phenyl-2-pyridyl)phenyl group, 4-(5-phenyl-2-pyridyl) Phenyl group, 2-(6-phenyl-2-pyridyl)phenyl group, 3-(6-phenyl-2-pyridyl)phenyl group, 4-(6-phenyl-2-pyridyl)phenyl group, 2-(2-phenyl -3-pyridyl)phenyl group, 3-(2-phenyl-3-pyridyl)phenyl group, 4-(2-phenyl-3-pyridyl)phenyl group, 2-(4-phenyl-3-pyridyl)phenyl group, 3-(4-phenyl-3-pyridyl)phenyl group, 4-(4-phenyl-3-pyridyl)phenyl group, 2-(5-phenyl-3-pyridyl)phenyl group, 3-(5-phenyl-3 -pyridyl)phenyl group, 4-(5-phenyl-3-pyridyl)phenyl group, 2-(6-phenyl-3-pyridyl)phenyl group, 3-(6-phenyl-3-pyridyl)phenyl group, 4- (6-phenyl-3-pyridyl)phenyl group, 2-(2-phenyl-4-pyridyl)phenyl group, 3-(2-phenyl-4-pyridyl)phenyl group, 4-(2-phenyl-4-pyridyl) dil)phenyl group, 2-(3-phenyl-4-pyridyl)phenyl group, 3-(3-phenyl-4-pyridyl)phenyl group, 4-(3-phenyl-4-pyridyl)phenyl group, 2-(2 ,4-diphenyl-3-pyridyl)phenyl group, 3-(2,4-diphenyl-3-pyridyl)phenyl group, 4-(2,4-diphenyl-3-pyridyl)phenyl group, 2-( 3,5-diphenyl-4-pyridyl)phenyl group, 3-(3,5-diphenyl-4-pyridyl)phenyl group, 4-(3,5-diphenyl-4-pyridyl)phenyl group,

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-(1-phenanthryl)phenyl group, 3-(1-phenanthryl)phenyl group, 4-(1-phenanthryl)phenyl group, 2-(2-phenanthryl)phenyl group, 3-(2-phenanthryl)phenyl group, 4-(2-phenanthryl)phenyl group, 2-(3-phenanthryl)phenyl group, 3-(3-phenanthryl)phenyl group, 4-(3-phenanthryl)phenyl group, 2-(4-phenanthryl)phenyl group, 3-(4-phenanthryl)phenyl group, 4-(4-phenanthryl)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, 2-(4-pyrenyl)phenyl group, 3-(4-pyrenyl)phenyl group, 4-(4-pyrenyl)phenyl group, 2-(fluoranten-1-yl ) Phenyl group, 3-(fluoranten-1-yl)phenyl group, 4-(fluoranten-1-yl)phenyl group, 2-(fluoranten-2-yl)phenyl group, 3-(fluoranthene-2 -yl)phenyl group, 4-(fluoranten-2-yl)phenyl group, 2-(fluoranten-3-yl)phenyl group, 3-(fluoranten-3-yl)phenyl group, 4-(fluoranthene -3-yl)phenyl group, 2-(fluoranten-4-yl)phenyl group, 3-(fluoranten-4-yl)phenyl group, 4-(fluoranten-4-yl)phenyl group, 2-(fluoro Lanten-5-yl)phenyl group, 3-(fluoranten-5-yl)phenyl group, 4-(fluoranten-5-yl)phenyl group, 2-(triphenylen-1-yl)phenyl group, 3- (triphenylen-1-yl)phenyl group, 4-(triphenylen-1-yl)phenyl group, 2-(triphenylen-2-yl)phenyl group, 3-(triphenylen-2-yl)phenyl group, 4-(triphenylen-2-yl)phenyl group, 2-(chrysen-1-yl)phenyl group, 3-(chrysen-1-yl)phenyl group, 4-(chrysen-1-yl)phenyl group, 2 -(Chryssen- 2-yl)phenyl group, 3-(chrysen-2-yl)phenyl group, 4-(chrysen-2-yl)phenyl group, 2-(chrysen-3-yl)phenyl group, 3-(chrysen-3- yl)phenyl group, 4-(chrysen-3-yl)phenyl group, 2-(chrysen-4-yl)phenyl group, 3-(chrysen-4-yl)phenyl group, 4-(chrysen-4-yl) Phenyl group, 2-(chrysen-5-yl)phenyl group, 3-(chrysen-5-yl)phenyl group, 4-(chrysen-5-yl)phenyl group, 2-(chrysen-6-yl)phenyl group, 3-(chrysen-6-yl)phenyl group, 4-(chrysen-6-yl)phenyl group, 2-(acenaphthylene-1-yl)phenyl group, 3-(acenaphthylene-1-yl)phenyl group, 4-(acenaphthylene-1-yl)phenyl group, 2-(acenaphthylene-3-yl)phenyl group, 3-(acenaphthylene-3-yl)phenyl group, 4-(acenaphthylene-3-yl) Phenyl group, 2-(acenaphthylene-4-yl)phenyl group, 3-(acenaphthylene-4-yl)phenyl group, 4-(acenaphthylene-4-yl)phenyl group, 2-(acenaphthylene-5- yl) phenyl group, 3-(acenaphthylene-5-yl)phenyl group, 4-(acenaphthylene-5-yl)phenyl group,

2-(fluoren-1-yl)phenyl group, 3-(fluoren-1-yl)phenyl group, 4-(fluoren-1-yl)phenyl group, 2-(fluoren-2-yl)phenyl group, 3- (fluoren-2-yl)phenyl group, 4-(fluoren-2-yl)phenyl group, 2-(fluoren-3-yl)phenyl group, 3-(fluoren-3-yl)phenyl group, 4-(flu Oren-3-yl)phenyl group, 2-(fluoren-4-yl)phenyl group, 3-(fluoren-4-yl)phenyl group, 4-(fluoren-4-yl)phenyl group, 2-(pyrimidine- 2-yl)phenyl group, 3-(pyrimidin-2-yl)phenyl group, 4-(pyrimidin-2-yl)phenyl group, 2-(pyrimidin-4-yl)phenyl group, 3-(pyrimidin-4- yl)phenyl group, 4-(pyrimidin-4-yl)phenyl group, 2-(pyrimidin-5-yl)phenyl group, 3-(pyrimidin-5-yl)phenyl group, 4-(pyrimidin-5-yl) Phenyl group, 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, 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-(2-isoquinolyl)phenyl group, 3-(2-isoquinolyl)phenyl group, 4-(2-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-iso Quinolyl)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, 4-(8-isoqui Nolyl) phenyl group, 2-(phenanthridin-2-yl) phenyl group, 3-(phenanthridin-2-yl) phenyl group, 4-(phenanthridin-2-yl) phenyl group, 2-(phenanthridine- 3-yl)phenyl group, 3-(phenanthridin-3-yl)phenyl group, 4-(phenanthridin-3-yl)phenyl group, 2-(phenanthridin-4-yl)phenyl group, 3-(phenantri Din-4-yl) phenyl group, 4- (phenanthridin-4-yl) phenyl group, 2- (phenanthridin-5-yl) phenyl group, 3- (phenanthridin-5-yl) phenyl group, 4- ( Phenanthridin-5-yl)phenyl group, 2-(phenanthridin-6-yl)phenyl group, 3-(phenanthridin-6-yl)phenyl group, 4-(phenanthridin-6-yl)phenyl group, 2 -(Phenanthridin-7-yl)phenyl group, 3-(phenanthridin-7-yl)phenyl group, 4-(phenanthridin-7-yl)phenyl group, 2-(phenanthridin-8-yl)phenyl group , 3-(phenanthridin-8-yl)phenyl group, 4-(phenanthridin-8-yl)phenyl group, 2-(phenanthridin-9-yl)phenyl group, 3-(phenanthridin-9-yl) ) Phenyl group, 4-(phenanthridine-9-yl)phenyl group, 2-(phenanthridine-10-yl)phenyl group, 3-(phenanthridine-10-yl)phenyl group, 4-(phenanthridine-10 -yl) phenyl group,

2-(benzo[h]quinolin-2-yl)phenyl group, 3-(benzo[h]quinolin-2-yl)phenyl group, 4-(benzo[h]quinolin-2-yl)phenyl group, 2-(benzo[ h]quinolin-3-yl)phenyl group, 3-(benzo[h]quinolin-3-yl)phenyl group, 4-(benzo[h]quinolin-3-yl)phenyl group, 2-(benzo[h]quinoline-4 -yl)phenyl group, 3-(benzo[h]quinolin-4-yl)phenyl group, 4-(benzo[h]quinolin-4-yl)phenyl group, 2-(benzo[h]quinolin-5-yl)phenyl group, 3-(benzo[h]quinolin-5-yl)phenyl group, 4-(benzo[h]quinolin-5-yl)phenyl group, 2-(benzo[h]quinolin-6-yl)phenyl group, 3-(benzo[ h]quinolin-6-yl)phenyl group, 4-(benzo[h]quinolin-6-yl)phenyl group, 2-(benzo[h]quinolin-7-yl)phenyl group, 3-(benzo[h]quinoline-7 -yl)phenyl group, 4-(benzo[h]quinolin-7-yl)phenyl group, 2-(benzo[h]quinolin-8-yl)phenyl group, 3-(benzo[h]quinolin-8-yl)phenyl group, 4-(benzo[h]quinolin-8-yl)phenyl group, 2-(benzo[h]quinolin-9-yl)phenyl group, 3-(benzo[h]quinolin-9-yl)phenyl group, 4-(benzo[ h]quinolin-9-yl)phenyl group, 2-(benzo[h]quinolin-10-yl)phenyl group, 3-(benzo[h]quinolin-10-yl)phenyl group, 4-(benzo[h]quinoline-10 -yl)phenyl group, 2-(acridin-1-yl)phenyl group, 3-(acridin-1-yl)phenyl group, 4-(acridin-1-yl)phenyl group, 2-(acridine -2-yl)phenyl group, 3-(acridin-2-yl)phenyl group, 4-(acridin-2-yl)phenyl group, 2-(acridin-3-yl)phenyl group, 3-(acridin-2-yl)phenyl group Creidin-3-yl)phenyl group, 4-(acridin-3-yl)phenyl group, 2-(acridin-4-yl)phenyl group, 3-(acridin-4-yl)phenyl group, 4- (acridin-4-yl)phenyl group, 2-(acridin-9-yl)phenyl group, 3-(acridin-9-yl)phenyl group, 4-(acridin-9-yl)phenyl group, 2-(2-thienyl)phenyl group, 3-(2-thienyl)phenyl group, 4-(2-thienyl)phenyl group, 2-(3-thienyl)phenyl group, 3-(3-thienyl)phenyl group, 4-(3-thienyl)phenyl group, 2-(3-methylthiophen-2-yl)phenyl group, 3-(3-methylthiophen-2-yl)phenyl group, 4-(3-methylthiophen-2 -yl)phenyl group, 2-(4-methylthiophen-2-yl)phenyl group, 3-(4-methylthiophene- 2-yl)phenyl group, 4-(4-methylthiophen-2-yl)phenyl group, 2-(5-methylthiophen-2-yl)phenyl group, 3-(5-methylthiophen-2-yl)phenyl group , 4-(5-methylthiophen-2-yl)phenyl group, 2-(2-methylthiophen-3-yl)phenyl group, 3-(2-methylthiophen-3-yl)phenyl group, 4-(2 -Methylthiophen-3-yl)phenyl group, 2-(4-methylthiophen-3-yl)phenyl group, 3-(4-methylthiophen-3-yl)phenyl group, 4-(4-methylthiophene- 3-yl)phenyl group, 2-(5-methylthiophen-3-yl)phenyl group, 3-(5-methylthiophen-3-yl)phenyl group, 4-(5-methylthiophen-3-yl)phenyl group , 2-(3-phenylthiophen-2-yl)phenyl group, 3-(3-phenylthiophen-2-yl)phenyl group, 4-(3-phenylthiophen-2-yl)phenyl group, 2-(4 -Phenylthiophen-2-yl)phenyl group, 3-(4-phenylthiophen-2-yl)phenyl group, 4-(4-phenylthiophen-2-yl)phenyl group, 2-(5-phenylthiophene- 2-yl)phenyl group, 3-(5-phenylthiophen-2-yl)phenyl group, 4-(5-phenylthiophen-2-yl)phenyl group, 2-(2-phenylthiophen-3-yl)phenyl group , 3-(2-phenylthiophen-3-yl)phenyl group, 4-(2-phenylthiophen-3-yl)phenyl group, 2-(4-phenylthiophen-3-yl)phenyl group, 3-(4 -Phenylthiophen-3-yl)phenyl group, 4-(4-phenylthiophen-3-yl)phenyl group, 2-(5-phenylthiophen-3-yl)phenyl group, 3-(5-phenylthiophene- 3-yl)phenyl group, 4-(5-phenylthiophen-3-yl)phenyl group,

3-(2-furyl)phenyl group, 4-(2-furyl)phenyl group, 2-(3-furyl)phenyl group, 3-(3-furyl)phenyl group, 4-(3-furyl)phenyl group, 2-(3- Methylfuran-2-yl)phenyl group, 3-(3-methylfuran-2-yl)phenyl group, 4-(3-methylfuran-2-yl)phenyl group, 2-(4-methylfuran-2-yl)phenyl group , 3-(4-methylfuran-2-yl)phenyl group, 4-(4-methylfuran-2-yl)phenyl group, 2-(5-methylfuran-2-yl)phenyl group, 3-(5-methylfuran -2-yl)phenyl group, 4-(5-methylfuran-2-yl)phenyl group, 2-(2-methylfuran-3-yl)phenyl group, 3-(2-methylfuran-3-yl)phenyl group, 4 -(2-methylfuran-3-yl)phenyl group, 2-(4-methylfuran-3-yl)phenyl group, 3-(4-methylfuran-3-yl)phenyl group, 4-(4-methylfuran-3 -yl)phenyl group, 2-(5-methylfuran-3-yl)phenyl group, 3-(5-methylfuran-3-yl)phenyl group, 4-(5-methylfuran-3-yl)phenyl group, 2-( 3-phenylfuran-2-yl)phenyl group, 3-(3-phenylfuran-2-yl)phenyl group, 4-(3-phenylfuran-2-yl)phenyl group, 2-(4-phenylfuran-2-yl) ) Phenyl group, 3-(4-phenylfuran-2-yl)phenyl group, 4-(4-phenylfuran-2-yl)phenyl group, 2-(5-phenylfuran-2-yl)phenyl group, 3-(5- Phenylfuran-2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 2-(2-phenylfuran-3-yl)phenyl group, 3-(2-phenylfuran-3-yl)phenyl group , 4-(2-phenylfuran-3-yl)phenyl group, 2-(4-phenylfuran-3-yl)phenyl group, 3-(4-phenylfuran-3-yl)phenyl group, 4-(4-phenylfuran -3-yl)phenyl group, 2-(5-phenylfuran-3-yl)phenyl group, 3-(5-phenylfuran-3-yl)phenyl group, 4-(5-phenylfuran-3-yl)phenyl group, 2 -(2-benzo[b]thienyl)phenyl group, 3-(2-benzo[b]thienyl)phenyl group, 4-(2-benzo[b]thienyl)phenyl group, 2-(3-benzo[b] Thienyl)phenyl group, 3-(3-benzo[b]thienyl)phenyl group, 4-(3-benzo[b]thienyl)phenyl group, 2-(4-benzo[b]thienyl)phenyl group, 3-( 4-benzo[b]thienyl)phenyl group, 4-(4-benzo[b]thienyl)phenyl group, 2-(5-benzo[b]thienyl)phenyl group, 3-(5-benzo[b]thienyl) ) phenyl group, 4- (5-benzo [b] thienyl) phenyl group, 2- (6-benzo [b] thienyl) phenyl group, 3- (6 -Benzo[b]thienyl)phenyl group, 4-(6-benzo[b]thienyl)phenyl group, 2-(7-benzo[b]thienyl)phenyl group, 3-(7-benzo[b]thienyl) Phenyl group, 4-(7-benzo[b]thienyl)phenyl group, 2-(2-benzo[b]furyl)phenyl group, 3-(2-benzo[b]furyl)phenyl group, 4-(2-benzo[b ]furyl)phenyl group, 2-(3-benzo[b]furyl)phenyl group, 3-(3-benzo[b]furyl)phenyl group, 4-(3-benzo[b]furyl)phenyl group, 2-(4-benzo [b] furyl) phenyl group, 3-(4-benzo [b] furyl) phenyl group, 4-(4-benzo [b] furyl) phenyl group, 2-(5-benzo [b] furyl) phenyl group, 3-(5 -Benzo[b]furyl)phenyl group, 4-(5-benzo[b]furyl)phenyl group, 2-(6-benzo[b]furyl)phenyl group, 3-(6-benzo[b]furyl)phenyl group, 4- (6-benzo [b] furyl) phenyl group, 2-(7-benzo [b] furyl) phenyl group, 3-(7-benzo [b] furyl) phenyl group, 4-(7-benzo [b] furyl) phenyl group, 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, 2-(1-di Benzofuryl)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-dibenzo furyl) phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group,

3-(2-pyridyl)biphenyl-4-yl group, 2'-(2-pyridyl)biphenyl-4-yl group, 4'-(2-pyridyl)biphenyl-4-yl group, 2,2 '-di(2-pyridyl)biphenyl-4-yl group, 2',4',6'-tri(2-pyridyl)biphenyl-4-yl group, 6-(2-pyridyl)biphenyl- 3-yl group, 5-(2-pyridyl)biphenyl-3-yl group, 2'-(2-pyridyl)biphenyl-3-yl group, 4'-(2-pyridyl)biphenyl-3-yl group , 6,2'-di (2-pyridyl) biphenyl-3-yl group, 5- (2-pyridyl) biphenyl-2-yl group, 6- (2-pyridyl) biphenyl-2-yl group, 2'-(2-pyridyl)biphenyl-2-yl group, 4'-(2-pyridyl)biphenyl-2-yl group, 6,2'-di(2-pyridyl)biphenyl-2-yl group , 3-(3-pyridyl)biphenyl-4-yl group, 2'-(3-pyridyl)biphenyl-4-yl group, 4'-(3-pyridyl)biphenyl-4-yl group, 2, 2'-di(3-pyridyl)biphenyl-4-yl group, 2',4',6'-tri(3-pyridyl)biphenyl-4-yl group, 6-(3-pyridyl)biphenyl -3-yl group, 5-(3-pyridyl)biphenyl-3-yl group, 2'-(3-pyridyl)biphenyl-3-yl group, 4'-(3-pyridyl)biphenyl-3- Diyl, 6,2'-di(3-pyridyl)biphenyl-3-yl group, 5-(3-pyridyl)biphenyl-2-yl group, 6-(3-pyridyl)biphenyl-2-yl group , 2'-(3-pyridyl)biphenyl-2-yl group, 4'-(3-pyridyl)biphenyl-2-yl group, 6,2'-di(3-pyridyl)biphenyl-2- Diyl, 3-(4-pyridyl)biphenyl-4-yl group, 2'-(4-pyridyl)biphenyl-4-yl group, 4'-(4-pyridyl)biphenyl-4-yl group, 2 , 2'-di (4-pyridyl) biphenyl-4-yl group, 2', 4 ', 6'-tri (4-pyridyl) biphenyl-4-yl group, 6- (4-pyridyl) bi Phenyl-3-yl group, 5-(4-pyridyl)biphenyl-3-yl group, 2'-(4-pyridyl)biphenyl-3-yl group, 4'-(4-pyridyl)biphenyl-3 -yl group, 6,2'-di(4-pyridyl)biphenyl-3-yl group, 5-(4-pyridyl)biphenyl-2-yl group, 6-(4-pyridyl)biphenyl-2- Diyl, 2'-(4-pyridyl)biphenyl-2-yl group, 4'-(4-pyridyl)biphenyl-2-yl group, 6,2'-di(4-pyridyl)biphenyl-2 -diary, 3-(1-naph Tyl) biphenyl-4-yl group, 2'-(1-naphthyl) biphenyl-4-yl group, 4'-(1-naphthyl) biphenyl-4-yl group, 2,2'-di (1- Naphthyl) biphenyl-4-yl group, 2', 4', 6'-tri (1-naphthyl) biphenyl-4-yl group, 6- (1-naphthyl) biphenyl-3-yl group, 5- (1-naphthyl) biphenyl-3-yl group, 2'-(1-naphthyl) biphenyl-3-yl group, 4'-(1-naphthyl) biphenyl-3-yl group, 6,2'- Di (1-naphthyl) biphenyl-3-yl group, 5- (1-naphthyl) biphenyl-2-yl group, 6- (1-naphthyl) biphenyl-2-yl group, 2'- (1- Naphthyl) biphenyl-2-yl group, 4'- (1-naphthyl) biphenyl-2-yl group, 6,2'-di (1-naphthyl) biphenyl-2-yl group, 3- (2- Naphthyl) biphenyl-4-yl group, 2'-(2-naphthyl) biphenyl-4-yl group, 4'-(2-naphthyl) biphenyl-4-yl group, 2,2'-di (2 -naphthyl) biphenyl-4-yl group, 2', 4', 6'-tri (2-naphthyl) biphenyl-4-yl group, 6- (2-naphthyl) biphenyl-3-yl group, 5 -(2-naphthyl)biphenyl-3-yl group, 2'-(2-naphthyl)biphenyl-3-yl group, 4'-(2-naphthyl)biphenyl-3-yl group, 6,2' -di(2-naphthyl)biphenyl-3-yl group, 5-(2-naphthyl)biphenyl-2-yl group, 6-(2-naphthyl)biphenyl-2-yl group, 2'-(2 -naphthyl) biphenyl-2-yl group, 4'-(2-naphthyl) biphenyl-2-yl group, 6,2'-di (2-naphthyl) biphenyl-2-yl group,

1-naphthyl group, 2-naphthyl group, 1-phenylnaphthylene-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalen-4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenyl Naphthalen-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-methylnaphthalene -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, 1-phenanthryl group , 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-phenylphenanthren-2-yl group, 1-phenylphenanthren-3-yl group, 1-phenylphenanthrene -4-yl group, 1-phenylphenanthren-5-yl group, 1-phenylphenanthren-6-yl group, 1-phenylphenanthren-7-yl group, 1-phenylphenanthren-8-yl group, 1-phenylphenanthrene -9-yl group, 1-phenylphenanthren-10-yl group, 2-phenylphenanthren-1-yl group, 2-phenylphenanthren-3-yl group, 2-phenylphenanthren-4-yl group, 2-phenylphenanthrene -5-yl group, 2-phenylphenanthren-6-yl group, 2-phenylphenanthren-7-yl group, 2-phenylphenanthren-8-yl group, 2-phenylphenanthren-9-yl group, 2-phenylphenanthrene -10-yl group, 3-phenylphenanthren-1-yl group, 3-phenylphenanthren-2-yl group, 3-phenylphenanthren-4-yl group, 3-phenylphenanthren-5-yl group, 3-phenylphenanthrene -6-yl group, 3-phenylphenanthren-7-yl group, 3-phenylphenanthren-8-yl group, 3-phenylphenanthren-9-yl group, 3-phenylphenanthren-10-yl group, 4-phenylphenanthrene -1-yl group, 4-phenylphenanthren-2-yl group, 4-phenylphenanthren-3-yl group, 4-phenylphenanthren-5-yl group, 4-phenylphenanthren-6-yl group, 4-phenylphenanthrene -7-yl group, 4-phenylphenanthren-8-yl group, 4-phenylphenanthren-9-yl group, 4-phenylphenanthren-10-yl group, 1-methylphenate Nanthren-2-yl group, 1-methylphenanthren-3-yl group, 1-methylphenanthren-4-yl group, 1-methylphenanthren-5-yl group, 1-methylphenanthren-6-yl group, 1-methyl Phenanthren-7-yl group, 1-methylphenanthren-8-yl group, 1-methylphenanthren-9-yl group, 1-methylphenanthren-10-yl group, 2-methylphenanthren-1-yl group, 2-methyl Phenanthren-3-yl group, 2-methylphenanthren-4-yl group, 2-methylphenanthren-5-yl group, 2-methylphenanthren-6-yl group, 2-methylphenanthren-7-yl group, 2-methyl Phenanthren-8-yl group, 2-methylphenanthren-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methylphenanthren-2-yl group, 3-methyl Phenanthren-4-yl group, 3-methylphenanthren-5-yl group, 3-methylphenanthren-6-yl group, 3-methylphenanthren-7-yl group, 3-methylphenanthren-8-yl group, 3-methyl Phenanthren-9-yl group, 3-methylphenanthren-10-yl group, 4-methylphenanthren-1-yl group, 4-methylphenanthren-2-yl group, 4-methylphenanthren-3-yl group, 4-methyl Phenanthren-5-yl group, 4-methylphenanthren-6-yl group, 4-methylphenanthren-7-yl group, 4-methylphenanthren-8-yl group, 4-methylphenanthren-9-yl group, 4-methyl phenanthrene-10 - diary,

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-phenylanthracene- 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, 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, 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- Diyl, 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-phenyl Pyren-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-methylpyrene -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 - diary, 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- Diyl, 9-methylpyren-8-yl group, 9-methylpyren-10-yl group, fluoranten-1-yl group, fluoranten-1-yl group, fluoranten-2-yl group, fluoranthene-3- Diyl, fluoranten-4-yl group, fluoranten-5-yl group, fluoranten-6-yl group, fluoranten-7-yl group, fluoranten-8-yl group, fluoranten-9-yl group, Fluoranthen-10-yl group, triphenylen-1-yl group, triphenylen-2-yl group, acenaphthylene-1-yl group, acenaphthylene-3-yl group, acenaphthylene-4-yl group, acenaph Tylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-iso Quinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, quinoxalin-2-yl group, quinoxalin-5-yl group, quinoxalin-6-yl group, quinazoline-2 -yl group, quinazolin-4-yl group, quinazolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-8-yl group, pyrazin-2-yl group, pyrimidin-2-yl group , pyrimidin-4-yl group, pyrimidin-5-yl group, acridin-1-yl group, acridin-1-yl group, acridin-2-yl group, acridin-3-yl group, acridine -4-yl group, acridin-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, phenantry Din-7-yl group, phenanthridin-8-yl group, phenanthridine-9-yl group, phenanthridin-10-yl group, phenazin-1-yl group, phenazin-2-yl group, benzo[h]quinoline- 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]quinoline- 7-yl group, benzo [h] quinolin-8-yl group, benzo [h] quinolin-9-yl group, benzo [h] quinolin-10-yl group, 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, benzothiophene-7- Diary, benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group, dibenzothiophene-1 -yl group, dibenzothiophen-2-yl group, dibenzothiophen-3-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, 3-methylthiophene -2-yl group, 4-methylthiophen-2-yl group, 5-methylthiophen-2-yl group, 2-methylthiophen-3-yl group, 4-methylthiophen-3-yl group, 5-methylthiophene -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, 3-methylbenzothiophen-2-yl group, 4-methylbenzothiophen-2-yl group, 5-methylbenzothiophen-2-yl group, 6-methylbenzothiophene-2 -yl group, 7-methylbenzothiophen-2-yl group, 2-methylbenzothiophen-3-yl group, 4-methylbenzothiophen-3-yl group, 5-methylbenzothiophen-3-yl group, 6-methyl Benzothiophen-3-yl group, 7-methylbenzothiophen-3-yl group, 2-methylbenzothiophen-4-yl group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4- Diyl, 6-methylbenzothiophen-4-yl group, 7-methylbenzothiophen-4-yl group, 2-methylbenzothiophen-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzo Thiophen-5-yl group, 6-methylbenzothiophen-5-yl group, 7-methylbenzothio phen-5-yl group, 2-methylbenzothiophen-6-yl group, 3-methylbenzothiophen-6-yl group, 4-methylbenzothiophen-6-yl group, 5-methylbenzothiophen-6-yl group, 7-methylbenzothiophen-6-yl group, 2-methylbenzothiophen-7-yl group, 3-methylbenzothiophen-7-yl group, 4-methylbenzothiophen-7-yl group, 5-methylbenzothiophene -7-yl group, 6-methylbenzothiophen-7-yl group, 3-methylbenzofuran-2-yl group, 4-methylbenzofuran-2-yl group, 5-methylbenzofuran-2-yl group, 6-methylbenzo Furan-2-yl group, 7-methylbenzofuran-2-yl group, 2-methylbenzofuran-3-yl group, 4-methylbenzofuran-3-yl group, 5-methylbenzofuran-3-yl group, 6-methylbenzo Furan-3-yl group, 7-methylbenzofuran-3-yl group, 2-methylbenzofuran-4-yl group, 3-methylbenzofuran-4-yl group, 5-methylbenzofuran-4-yl group, 6-methylbenzo Furan-4-yl group, 7-methylbenzofuran-4-yl group, 2-methylbenzofuran-5-yl group, 3-methylbenzofuran-5-yl group, 4-methylbenzofuran-5-yl group, 6-methylbenzo Furan-5-yl group, 7-methylbenzofuran-5-yl group, 2-methylbenzofuran-6-yl group, 3-methylbenzofuran-6-yl group, 4-methylbenzofuran-6-yl group, 5-methylbenzo Furan-6-yl group, 7-methylbenzofuran-6-yl group, 2-methylbenzofuran-7-yl group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methylbenzo Furan-7-yl group, 6-methylbenzofuran-7-yl group, 2-methyldibenzothiophen-1-yl group, 3-methyldibenzothiophen-1-yl group, 4-methyldibenzothiophen-1-yl group diyl group, 6-methyldibenzothiophen-1-yl group, 7-methyldibenzothiophen-1-yl group, 8-methyldibenzothiophen-1-yl group, 9-methyldibenzothiophen-1-yl group, 1-methyldibenzothiophen-2-yl group, 3-methyldibenzothiophen-2-yl group, 4-methyldibenzothiophen-2-yl group, 6-methyldibenzothiophen-2-yl group, 7- Methyldibenzothiophen-2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyldibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldi Benzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group, 7-methyldibenzothiophen-3-yl group, 8-methyldibenzothi Offen-3-yl group, 9-methyldibenzothiophen-3-yl group, 2-methyl Dibenzofuran-1-yl group, 3-methyldibenzofuran-1-yl group, 4-methyldibenzofuran-1-yl group, 6-methyldibenzofuran-1-yl group, 7-methyldibenzofuran-1-yl group Diyl, 8-methyldibenzofuran-1-yl group, 9-methyldibenzofuran-1-yl group, 1-methyldibenzofuran-2-yl group, 3-methyldibenzofuran-2-yl group, 4-methyldi Benzofuran-2-yl group, 6-methyldibenzofuran-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-methyldibenzo Furan-3-yl group, 8-methyldibenzofuran-3-yl group, 9-methyldibenzofuran-3-yl group, 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, 3-phenylfuran-2-yl group, 4-phenyl Furan-2-yl group, 5-phenylfuran-2-yl group, 2-phenylfuran-3-yl group, 4-phenylfuran-3-yl group, 5-phenylfuran-3-yl group, 3-phenylbenzothiophene-2 -yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7-phenylbenzothiophen-2-yl group, 2-phenyl Benzothiophen-3-yl group, 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophen-3-yl group, 7-phenylbenzothiophene-3- Diyl, 2-phenylbenzothiophen-4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenylbenzothiophen-4-yl group, 7-phenylbenzo Thiophen-4-yl group, 2-phenylbenzothiophen-5-yl group, 3-phenylbenzothiophen-5-yl group, 4-phenylbenzothiophen-5-yl group, 6-phenylbenzothiophen-5-yl group , 7-phenylbenzothiophen-5-yl group, 2-phenylbenzothiophen-6-yl group, 3-phenylbenzothiophen-6-yl group, 4-phenylbenzothiophen-6-yl group, 5-phenylbenzothi Offen-6-yl group, 7-phenylbenzothiophen-6-yl group, 2-phenylbenzothiophen-7-yl group, 3-phenylbenzothiophen-7-yl group, 4-phenylbenzothiophen-7-yl group, 5-phenylbenzothiophen-7-yl group, 6-phenylbenzothiophen-7-yl group, 3-phenylbene Zofuran-2-yl group, 4-phenylbenzofuran-2-yl group, 5-phenylbenzofuran-2-yl group, 6-phenylbenzofuran-2-yl group, 7-phenylbenzofuran-2-yl group, 2-phenyl Benzofuran-3-yl group, 4-phenylbenzofuran-3-yl group, 5-phenylbenzofuran-3-yl group, 6-phenylbenzofuran-3-yl group, 7-phenylbenzofuran-3-yl group, 2-phenyl Benzofuran-4-yl group, 3-phenylbenzofuran-4-yl group, 5-phenylbenzofuran-4-yl group, 6-phenylbenzofuran-4-yl group, 7-phenylbenzofuran-4-yl group, 2-phenyl Benzofuran-5-yl group, 3-phenylbenzofuran-5-yl group, 4-phenylbenzofuran-5-yl group, 6-phenylbenzofuran-5-yl group, 7-phenylbenzofuran-5-yl group, 2-phenyl Benzofuran-6-yl group, 3-phenylbenzofuran-6-yl group, 4-phenylbenzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6-yl group, 2-phenyl Benzofuran-7-yl group, 3-phenylbenzofuran-7-yl group, 4-phenylbenzofuran-7-yl group, 5-phenylbenzofuran-7-yl group, 6-phenylbenzofuran-7-yl group, 2-phenyl Dibenzothiophen-1-yl group, 3-phenyldibenzothiophen-1-yl group, 4-phenyldibenzothiophen-1-yl group, 6-phenyldibenzothiophen-1-yl group, 7-phenyldibenzo Thiophen-1-yl group, 8-phenyldibenzothiophen-1-yl group, 9-phenyldibenzothiophen-1-yl group, 1-phenyldibenzothiophen-2-yl group, 3-phenyldibenzothiophene -2-yl group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group, 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophene-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,

2-phenyldibenzofuran-1-yl group, 3-phenyldibenzofuran-1-yl group, 4-phenyldibenzofuran-1-yl group, 6-phenyldibenzofuran-1-yl group, 7-phenyldibenzofuran group -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-yl group, 6-phenyldibenzofuran-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, 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)thi Offen-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, 3-(2-pyridyl)benzothiophen-2-yl group, 4-(2-pyridyl)benzothiophen-2-yl group, 5-(2-pyridyl)benzothiophene-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-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-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, 6-(2-pyridyl) )benzothiophen-7-yl group, 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-pyri dil) 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, 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-pyri dil)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, 6-(2-pyri dil) benzofuran-7-yl group, 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-pyri Diyl) dibenzothiophen-1-yl group, 9-(2-pyridyl) dibenzothiophen-1-yl group, 1-(2-pyridyl) dibenzothiophen-2-yl group, 3-(2- Pipe Diyl) dibenzothiophen-2-yl group, 4- (2-pyridyl) dibenzothiophen-2-yl group, 6- (2-pyridyl) 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,

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-pyri Diyl) dibenzofuran-2-yl group, 6-(2-pyridyl)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)dibenzo Furan-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, 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, 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, 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)benzothi Offen-3-yl group, 4-(3-pyridyl)benzothiophen-3-yl group, 5-(3-pyridyl)benzothiophen-3-yl group, 6-(3-pyridyl)benzothiophene- 3-yl group, 7-(3-pyridyl)benzothiophen-3-yl group, 2-(3-pyridyl)benzothiophen-4-yl group, 3-(3-pyridyl)benzothiophen-4- diyl, 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-yl group, 4-(3-pyridyl)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)benzo Thiophen-7-yl group, 5-(3-pyridyl)benzothiophen-7-yl group, 6-(3-pyridyl)benzothiophen-7-yl group, 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-pyri dil) 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, 2-(3-pyridyl)benzofuran-5-yl group, 3-(3-pyridyl)benzofuran-5-yl group, 4-(3-pyri dil) 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-pyri dil)benzofuran-7-yl group, 5-(3-pyridyl)benzofuran-7-yl group, 6-(3-pyridyl)benzofuran-7-yl group, 2-(3-pyridyl)dibenzothi Offen-1-yl group, 3-(3-pyridyl)dibenzothiophen-1-yl group, 4-(3-pyridyl)dibenzothiophen-1-yl group, 6-(3-pyridyl)dibenzo thiophene- 1-yl group, 7-(3-pyridyl)dibenzothiophen-1-yl group, 8-(3-pyridyl)dibenzothiophen-1-yl group, 9-(3-pyridyl)dibenzothiophene -1-yl group, 1-(3-pyridyl)dibenzothiophen-2-yl group, 3-(3-pyridyl)dibenzothiophen-2-yl group, 4-(3-pyridyl)dibenzothi Offen-2-yl group, 6-(3-pyridyl)dibenzothiophen-2-yl group, 7-(3-pyridyl)dibenzothiophen-2-yl group, 8-(3-pyridyl)dibenzo Thiophen-2-yl group, 9-(3-pyridyl)dibenzothiophen-2-yl group, 1-(3-pyridyl)dibenzothiophen-3-yl group, 2-(3-pyridyl)di Benzothiophen-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, 2-(3-pyridyl ) Dibenzofuran-1-yl group, 3-(3-pyridyl)dibenzofuran-1-yl group, 4-(3-pyridyl)dibenzofuran-1-yl group, 6-(3-pyridyl)di Benzofuran-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-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, 3-(4-pyridyl) thiophen-2-yl group, 4-(4-pyri dil) thiophen-2-yl group, 5-(4-pyridyl) thiophen-2-yl group, 2-(4-pyridyl) thiophen-3-yl group, 4-(4-pyridyl) thiophene- 3-yl group, 5-(4-pyridyl)thiophen-3-yl group,

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, 5-(4-pyridyl)furan-3-yl group, 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-3-yl group, 6-(4-pyridyl)benzothiophen-3-yl group, 7-(4-pyridyl)benzothiophen-3-yl group, 2-(4-pyri dil)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)benzothi Offen-5-yl group, 4-(4-pyridyl)benzothiophen-5-yl group, 6-(4-pyridyl)benzothiophen-5-yl group, 7-(4-pyridyl)benzothiophene- 5-yl group, 2-(4-pyridyl)benzothiophen-6-yl group, 3-(4-pyridyl)benzothiophen-6-yl group, 4-(4-pyridyl)benzothiophen-6- diyl, 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, 6- (4-pyridyl)benzothiophen-7-yl group, 3-(4-pyridyl)benzofuran-2-yl group, 4-(4-pyridyl)benzofuran-2-yl group, 5-(4-pyri dil) 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-pyri dil) benzofuran-4-yl group, 6- (4-pyridyl)benzofuran-4-yl group, 7-(4-pyridyl)benzofuran-4-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, 6-(4-pyridyl)benzofuran-7 -yl group, 2-(4-pyridyl)dibenzothiophen-1-yl group, 3-(4-pyridyl)dibenzothiophen-1-yl group, 4-(4-pyridyl)dibenzothiophene- 1-yl group, 6-(4-pyridyl)dibenzothiophen-1-yl group, 7-(4-pyridyl)dibenzothiophen-1-yl group, 8-(4-pyridyl)dibenzothiophene -1-yl group, 9-(4-pyridyl)dibenzothiophen-1-yl group, 1-(4-pyridyl)dibenzothiophen-2-yl group, 3-(4-pyridyl)dibenzothi Offen-2-yl group, 4-(4-pyridyl)dibenzothiophen-2-yl group, 6-(4-pyridyl)dibenzothiophen-2-yl group, 7-(4-pyridyl)dibenzo Thiophen-2-yl group, 8-(4-pyridyl)dibenzothiophen-2-yl group, 9-(4-pyridyl)dibenzothiophen-2-yl group, 1-(4-pyridyl)di Benzothiophen-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,

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-pyri Dill) dibenzofuran-2-yl group, 6-(4-pyridyl)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)dibenzo Furan-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, 2-{8-(2-pyridyl)dibenzofuran -2-yl}phenyl group, 3-{8-(2-pyridyl)dibenzofuran-2-yl}phenyl group, 4-{8-(2-pyridyl)dibenzofuran-2-yl}phenyl group, 2 -{8-(3-pyridyl)dibenzofuran-2-yl}phenyl group, 3-{8-(3-pyridyl)dibenzofuran-2-yl}phenyl group, 4-{8-(3-pyri diyl) dibenzofuran-2-yl}phenyl group, 2-{8-(4-pyridyl)dibenzofuran-2-yl}phenyl group, 3-{8-(4-pyridyl)dibenzofuran-2- yl}phenyl group, 4-{8-(4-pyridyl)dibenzofuran-2-yl}phenyl group, 2-{8-(3-methyl-2-pyridyl)dibenzofuran-2-yl}phenyl group, 3-{8-(3-methyl-2-pyridyl)dibenzofuran-2-yl}phenyl group, 4-{8-(3-methyl-2-pyridyl)dibenzofuran-2-yl}phenyl group, 2-{8-(2-methyl-3-pyridyl)dibenzofuran-2-yl}phenyl group, 3-{8-(2-methyl-3-pyridyl)dibenzofuran-2-yl}phenyl group, 4-{8-(2-methyl-3-pyridyl)dibenzofuran-2-yl}phenyl group, 2-{8-(3-methyl-4-pyridyl)dibenzofuran-2-yl}phenyl group, 3-{8-(3-methyl-4-pyridyl)dibenzofuran-2-yl}phenyl group, 4-{8-(3-methyl-4-pyridyl)dibenzofuran Ran-2-yl}phenyl group, 2-{8-(2,6-dimethyl-3-pyridyl)dibenzofuran-2-yl}phenyl group, 3-{8-(2,6-dimethyl-3 -pyridyl) dibenzofuran-2-yl}phenyl group, 4-{8-(2,6-dimethyl-3-pyridyl)dibenzofuran-2-yl}phenyl group, 2-{8-(2- Pyrimidyl) dibenzofuran-2-yl}phenyl group, 3-{8-(2-pyrimidyl)dibenzofuran-2-yl}phenyl group, 4-{8-(2-pyrimidyl)dibenzofuran-2 -yl}phenyl group, 2-{8-(5-pyrimidyl)dibenzofuran-2-yl}phenyl group, 3-{8-(5-pyrimidyl)dibenzofuran-2-yl}phenyl group, 4-{ 8-(5-pyrimidyl)dibenzofuran-2-yl}phenyl group etc. are mentioned as a preferable example. Among these substituents, in view of excellent electron transporting material properties, phenyl group, p-tolyl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-(1-naphthyl)phenyl group, 3-(2-naph tyl)phenyl group, 4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 3-(fluoranthene) -3-yl)phenyl group, 4-(fluoranten-3-yl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 3-(2-quinolyl)phenyl group, 4-(2-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 3-(5-methylthiophen-2-yl)phenyl group, 4-(5-methylthiophen-2-yl)phenyl group, 3-(5-methylfuran-2-yl)phenyl group, 4-(5-methyl furan-2-yl)phenyl group, 3-(2-benzothienyl)phenyl group, 4-(2-benzothienyl)phenyl group, 3-(2-benzofuryl)phenyl group, 4-(2-benzofuryl)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-dibenzofuryl)phenyl group, 3-(4-dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 2-phenylpyridin-6-yl group , 2-phenylpyridin-5-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-5-yl group, 3-phenylpyridin-6-yl group, 5-phenylthiophen-2-yl group, 5-phenyl furan-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-benzothienyl group, 2-benzofuryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group Group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, 2-{8-(3-methyl-2-pyridyl)dibenzofuran-2 -yl}phenyl group, 3-{8-(3-methyl-2-pyridyl)dibenzofuran-2-yl}phenyl group, 2-{8-(2,6-dimethyl-3-pyridyl)dibenzo Furan-2-yl}phenyl group, 3-{8-(2,6-dimethyl-3-pyridyl)dibenzofuran-2-yl}phenyl group, 2-{8-(2-pyrimidyl)dibenzofuran A -2-yl}phenyl group, or a 3-{8-(2-pyrimidyl)dibenzofuran-2-yl}phenyl group is preferred High, phenyl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-(1-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 4- (2-naphthyl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)phenyl group, 3-(fluoranthen-3-yl)phenyl group, 4-(fluoranthene-3- yl)phenyl group, 3-(2-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 3-(2-qui Nolyl)phenyl group, 4-(2-quinolyl)phenyl group, 3-(3-quinolyl)phenyl group, 4-(3-quinolyl)phenyl group, 3-(2-benzothienyl)phenyl group, 4-(2- Benzothienyl)phenyl group, 3-(2-benzofuryl)phenyl group, 4-(2-benzofuryl)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-dibenzofuryl)phenyl group, 3-(4 -Dibenzofuryl)phenyl group, 4-(4-dibenzofuryl)phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4- A dibenzothienyl group, 4-dibenzofuryl group, etc. are more preferable.

A represents a single bond.

B ¹ and B ² represent a single bond or a hydrogen atom. However, either one of B ¹ or B ² represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.

Either one of Z ¹ and Z ² represents a nitrogen atom, and the other represents CH.

The compound represented by the general formula (1) can also be represented by the compound represented by the general formula (1a) or (1b) as follows:

(In general formulas (1a) and (1b), Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , Z ¹ and Z ² have the same definitions as in the general formula (1). )

In General Formulas (1a) and (1b), about the preferable range of each definition, it is the same as General formula (1).

When the triazine compound (1) of the present invention is used as a component of an organic electroluminescent device, effects such as high luminous efficiency, long life, and low voltage can be obtained. In particular, when it is used as an electron transport layer, this effect appears remarkably.

Among the compounds represented by the general formula (1), the following (A-1) to (A-960) can be exemplified as specific examples of particularly preferable compounds, but the present invention is not limited thereto.

Hereinafter, the usage method of a triazine compound (1) is demonstrated.

The light emitting layer in an organic electroluminescent element refers to the layer which emits light when electric current flows through the electrode which consists of a cathode and an anode in a broad meaning. Specifically, it refers to a layer containing a fluorescent compound that emits light when an electric current is passed through an electrode composed of a cathode and an anode. In general, an organic electroluminescent device has a structure in which a light emitting layer is inserted between a pair of electrodes.

The organic electroluminescent device of the present invention is provided with a hole transport layer, an electron transport layer, an anode buffer layer and a cathode buffer layer in addition to the light emitting layer if necessary, and takes a structure interposed between the cathode and the anode. Specifically, the structure shown below is mentioned.

(i) anode/light 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/anode buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode buffer layer/cathode.

A conventionally well-known light emitting material can be used for the light emitting layer in the organic electroluminescent element of this invention. As a method of forming a light emitting layer, there exists a method of forming a thin film by well-known methods, such as a vapor deposition method, a spin coating method, a casting method, and the LB method, for example.

In addition, this light emitting layer can be obtained by dissolving a light emitting material in a solvent together with binders, such as resin, to make a solution, then apply|coating this by the spin coating method etc. and forming a thin film.

There is no restriction|limiting in particular about the film thickness of the light emitting layer formed in this way, Although it can select suitably according to a situation, Usually, it is the range of 5 nm - 5 micrometers.

Next, other layers constituting the organic electroluminescent device in combination with the light emitting layer, such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, will be described.

The hole injection layer and the hole transport layer have a function of transferring the holes injected from the anode to the light emitting layer, and by interposing the hole injection layer and the hole transport layer between the anode and the light emitting layer, many holes are injected into the light emitting layer at a lower electric field.

In addition, electrons injected from the cathode and transported from the electron injection layer and/or the electron transport layer to the light emitting layer leak into the hole injection layer or the hole transport layer due to an electron barrier existing at the interface between the light emitting layer and the hole injection layer or the hole transport layer. It accumulates at the interface in the light emitting layer without becoming a luminescent layer, and it becomes an element excellent in light emitting performance, such as a light emitting efficiency improving.

The hole injection material and the hole transport material have any of hole injection or transport and electron barrier properties, and may be either an organic material or an inorganic material. Examples of the hole injection material and hole transport material include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and 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, and conductive polymer oligomers, particularly thiophene oligomers, and the like. . As the hole injecting material and the hole transporting material, the above can be used, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound, particularly an aromatic tertiary amine compound.

Representative examples of the aromatic tertiary amine compound and the styrylamine compound 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'-di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl Ter, 4,4'-bis(diphenylamino)quadrylphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di -p-tolyl amino) styryl] stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N -Phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), 4,4',4"-tris[N-(3-methylphenyl)- N-phenylamino]triphenylamine (MTDATA) etc. are mentioned.

Moreover, inorganic compounds, such as p-type-Si and p-type-SiC, can also be used as a hole injection material and a hole transport material. The hole injection layer and the hole transport layer can be formed by thinning the hole injection material and the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Although there is no restriction|limiting in particular about the film thickness of a positive hole injection layer and a positive hole transport layer, Usually, it is about 5 nm - 5 micrometers. The hole injection layer and the hole transport layer may have a single-layer structure composed of one or two or more of the above materials, or a laminate structure composed of a plurality of layers of the same composition or different compositions.

In the organic electroluminescent device of the present invention, the electron transport layer contains the triazine compound represented by the general formula (1).

The electron transport layer can be formed by forming a film of the triazine compound represented by the general formula (1) by, for example, a known thin film formation method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Although there is no restriction|limiting in particular in the film thickness of an electron carrying layer, Usually, it is selected in the range of 5 nm - 5 micrometers. Moreover, this electron transport layer may contain the triazine compound represented by General formula (1), and may also contain the conventionally well-known electron transport material, The single-layer structure which consists of 1 type or 2 or more types may be sufficient, or , may be a laminated structure composed of a plurality of layers of the same composition or different compositions.

Further, in the present invention, the light emitting material is not limited to only the light emitting layer, and one type may be contained in the hole transport layer or the electron transport layer adjacent to the light emitting layer, thereby further enhancing the luminous efficiency of the organic electroluminescent device.

The substrate preferably used for the organic electroluminescent device of the present invention is not particularly limited as to the type of glass, plastic, or the like, and is not particularly limited as long as it is transparent. Examples of the substrate preferably used for the organic electroluminescent device of the present invention include glass, quartz, and a light-transmitting plastic film.

Examples of the light-transmitting plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylenesulfide, and polyarylene. and films made of cellulose, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

A suitable example of manufacturing the organic electroluminescent device of the present invention will be described. As an example, a method for manufacturing an organic electroluminescent device including the anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode will be described.

First, on a suitable substrate, a thin film made of a desired electrode material, for example, an anode material, is deposited to a thickness in the range of 1 µm or less, preferably 10 to 200 nm, by vapor deposition or sputtering. to form an anode. Next, a thin film composed of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer/electron injection layer, which are element materials, is formed thereon.

Further, a buffer layer (electrode interface layer) may be provided between the anode and the light emitting layer or the hole injection layer and between the cathode and the light emitting layer or the electron injection layer.

Moreover, in addition to the said basic structural layer, you may laminate|stack the layer which has other functions as needed, for example, you may have functional layers, such as a hole block layer and an electron block layer.

Next, the electrode of the organic electroluminescent device of the present invention will be described. As the anode in the organic electroluminescent device, a metal having a large work function (4 eV or more), an alloy, an electrically conductive compound, and a mixture thereof are preferably used as the electrode material. Specific examples of the electrode material include metals such as Au, CuI, indium oxide-tin (ITO), SnO ₂ , and conductive transparent materials such as ZnO.

The anode may form a thin film of these electrode materials by a method such as vapor deposition or sputtering, and a pattern of a desired shape may be formed by a photolithography method, or a pattern may be formed through a mask of a desired shape during deposition or sputtering. also be

On the other hand, as the cathode, a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are preferably used as the electrode material. Specific examples of such an electrode material 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 ) mixture, indium, lithium/aluminum mixtures, rare earth metals, and the like. Among them, a mixture of an electron injecting metal and a second metal that is a stable metal having a larger work function value than this in terms of electron injecting properties and durability against oxidation, for example, a magnesium/silver mixture, a magnesium/aluminum mixture, Magnesium/indium mixtures, aluminum/aluminum oxide (Al ₂ O ₃ ) mixtures, lithium/aluminum mixtures and the like are suitable. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.

As described above, a method such as vapor deposition or sputtering to form a thin film made of a desired electrode material, for example, an anode material, on a suitable substrate to a film thickness in the range of 1 μm or less, preferably 10 to 200 nm. After forming an anode by forming an anode, a thin film composed of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer/electron injection layer is formed on the anode as described above, and then a thin film made of a material for a cathode thereon is formed by a method such as vapor deposition or sputtering so as to have a film thickness in the range of 1 µm or less, preferably 50 to 200 nm, and a cathode is provided to obtain a desired organic electroluminescent device.

The organic electroluminescent device of the present invention may be used as a lamp for illumination or as a kind of lamp such as an exposure light source, a projection device for projecting an image, or a display device (display) for directly viewing a still image or a moving image. do. When used as a display device for reproducing moving images, the driving method may be either a simple matrix (passive matrix) method, an active matrix method, or any other method. In addition, by using two or more types of organic electroluminescent elements of the present invention having different luminous colors, it is possible to manufacture a full-color display device.

[Brief Description of Drawings]

1 is a cross-sectional view of a single-layer device fabricated in Example.

[Explanation of code]

1. Glass substrate with ITO transparent electrode

2. hole injection layer

3. Charge generation layer

4. hole transport layer

5. Emissive layer

6. Electron transport layer

7. Cathode layer

Next, the manufacturing method of this invention is demonstrated.

The triazine compound (1) of the present invention can be prepared by the method represented by the following schemes (1) and (2) in the presence or absence of a base, in the presence of a palladium catalyst:

(In Scheme (1), Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² represent the same substituents as described above. Y represents a leaving group described later. M ¹ and M ² represent a substituent described later. )

(In Scheme (2), Ar ¹ , Ar ² , Ar ³ , Z ¹ and Z ² represent the same substituents as described above. Y ¹ and Y ² represent a leaving group described later. M represents a substituent described later. )

Hereinafter, the compound represented by the general formula (2) is referred to as a compound (2). In addition, it is set as synonymous also about compound (3) - compound (5). Hereinafter, the definition of these compounds is demonstrated.

Y represents a leaving group, and although it is not specifically limited, For example, a chlorine atom, a bromine atom, an iodine atom, a triflate, etc. are mentioned. Among these, a bromine atom or a chlorine atom is preferable at a point with a favorable reaction yield. However, in some cases, it is preferable to use a triplate from the viewpoint of the availability of raw materials. ^In addition, about Y1 and Y2, either ^{one of} Y1 or Y2 is synonymous with Y, and ^the other represents a hydrogen atom.

M each independently represents ZnR ¹ , MgR ² , Sn(R ³ ) ₃ or B(OR ⁴ ) ₂ . However, R ¹ and R ² each independently represent a chlorine atom, a bromine atom or an iodine atom, R ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, R ⁴ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms Or a phenyl group is shown, and two R< ⁴ > of B(OR ⁴ ) ₂ may be the same or different. In addition, two R ⁴ may be integrated to form a ring including an oxygen atom and a boron atom.

As ^ZnR1 and ^MgR2 , ZnCl, ZnBr, ZnI, MgCl, MgBr, MgI, etc. can be illustrated.

As Sn(R ₃ ) ₃ , Sn(Me) ₃ , Sn(Bu) ₃ , and the like can be exemplified.

Examples of B(OR ⁴ ) ₂ include B(OH) ₂ , B(OMe) ₂ , B(O ⁱ Pr) ₂ , B(OBu) ₂ , and the like. In addition, as an example of B(OR ⁴ ) ₂ when two R ⁴ are integrated to form a ring including an oxygen atom and a boron atom, groups represented by (C-1) to (C-6) It can be illustrated, and the group represented by (C-2) is preferable at a point with a favorable yield.

In addition, about M< ¹ > and M< ² >, either one of M< ¹ > or M< ² > is synonymous with said M, and the other represents a hydrogen atom.

Compound (3) used in Scheme (1) is, for example,

[0105] to [0121] of Japanese Unexamined Patent Publication No. 2005-268199, [0061] to [0076] of Japanese Unexamined Patent Application Publication No. 2008-280330, or [0076] of Japanese Unexamined Patent Publication No. 2001-335516 It can be prepared by combining the methods disclosed in 0047 to [0082]. As compound (3), although the following (B-1) - (B-56) can be illustrated, this invention is not limited to these.

Compound (5) used in Scheme (2) represents a compound in which M ¹ and M ² of the compound (3) are substituted with Y ¹ and Y ² , respectively. Specific examples of compound (5) include those obtained by substituting Y for M in the above (B-1) to (B-56), but the present invention is not limited thereto. In addition, the definitions of these M ¹ , M ² , Y ¹ , Y ² , M and Y are as described above.

Then, Reaction Formula (1) is demonstrated. "Step 1" is a method for obtaining the triazine compound (1) of the present invention by reacting compound (2) with compound (3) in the presence or absence of a base, in the presence of a palladium catalyst, Suzuki- Reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, and Stille reaction are applied By doing so, the target product can be obtained with good yield.

Examples of the palladium catalyst that can be used in "Step 1" include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. In addition, π-arylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium and dichloro (1 and complex compounds such as ,1'-bis(diphenylphosphino)ferrocene)palladium. Among them, a palladium complex having a tertiary phosphine as a ligand is more preferable in terms of a good reaction yield, and a palladium complex having a triphenylphosphine as a ligand is particularly preferable from the viewpoint of easy availability and good reaction yield. do.

A palladium complex having a tertiary phosphine as a ligand can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound. Examples of the tertiary phosphine that can be used at this time include triphenylphosphine, trimethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9, 9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(di-tert-butyl Phosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, bis(diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino) ) propane, 1,4-bis (diphenylphosphino) butane, 1,1'-bis (diphenylphosphino) ferrocene, tri (2-furyl) phosphine, tri (o-tolyl) phosphine, tris ( 2,5-xylyl)phosphine, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 2-dicyclohexylphosphino-2',4', 6'-triisopropylbiphenyl etc. can be illustrated. From the viewpoint of easy availability and good reaction yield, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl or triphenylphosphine is preferable. The molar ratio of the tertiary phosphine to the palladium salt or complex is preferably 1:10 to 10:1, more preferably 1:2 to 5:1 from the viewpoint of good reaction yield.

Examples of the base that can be used in "Step 1" include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, cesium fluoride, and the like. and potassium carbonate is preferable from the viewpoint of good yield. The molar ratio of the base to the compound (3) is preferably 1:2 to 10:1, and more preferably 1:1 to 3:1 in terms of good yield.

The molar ratio of compound (2) and compound (3) used in "Step 1" is preferably 1:2 to 5:1, and more preferably 1:2 to 2:1 in terms of good yield.

As a solvent that can be used in "Step 1", water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, methanol Or xylene etc. can be illustrated, and you may use these combining them suitably. It is preferable to use dioxane or a mixed solvent of THF and water from the viewpoint of good yield.

"Step 1" can be carried out at a temperature suitably selected from 0°C to 150°C, and it is more preferable to carry out at 50°C to 100°C from the viewpoint of good yield.

Compound (1) is obtained by performing a normal treatment after the completion of "Step 1". If necessary, you may refine|purify by recrystallization, column chromatography, sublimation, etc.

"Step 2" is a method for obtaining the triazine compound (1) of the present invention by reacting compound (4) with compound (5) in the presence or absence of a base, in the presence of a palladium catalyst, Suzuki- By applying the reaction conditions of general coupling reactions, such as the Miyaura reaction, the Negishi reaction, the Tamao-Kumada reaction, and the Stille reaction, the target product can be obtained in good yield.

In "Step 2", among the conditions in "Step 1", conditions for substituting compound (2) with compound (5) and compound (3) with compound (4) may be applied. However, it is not necessary to have the same reaction conditions as in "Step 1". After completion of "Step 2", if necessary, purification may be performed by recrystallization, column chromatography, sublimation, or the like.

The triazine compound (1) of the present invention can be suitably used as a material for an organic electroluminescent device.

In addition, the triazine compound (1) of this invention can be used suitably as an electron transport material for organic electroluminescent elements, or an electron injection material.

The triazine compound (1) of the present invention is effective when used as a part of a constituent component of an organic electroluminescent device. In particular, when used as an electron transport layer, effects such as longer life, higher efficiency and lower voltage can be obtained compared to conventional devices. Further, when the triazine compound (1) of the present invention is used as a material for an organic electroluminescent device, it can be used as a co-deposition film with any organometallic species, organic compound or inorganic compound.

Although there is no restriction|limiting in particular in the manufacturing method of the thin film for organic electroluminescent element which consists of the triazine compound (1) of this invention, The film-forming by the vacuum deposition method is possible. Film formation by the vacuum deposition method can be performed by using a general-purpose vacuum deposition apparatus. The degree of vacuum of the vacuum chamber when the film is formed by the vacuum deposition method is to be achieved by a diffusion pump, a turbo molecular pump, and a cryopump, which are generally used in consideration of the manufacturing time and manufacturing cost of manufacturing the organic electroluminescent device. It is preferably about 1×10 ^-2 Pa to 1×10 ^-5 Pa, more preferably 1×10 ^-3 to 10 ^-6 Pa. Although the deposition rate depends on the thickness of the film to be formed, 0.005 to 1.0 nm/sec is preferable, and more preferably 0.01 to 1 nm/sec. In addition, since the triazine compounds (11) and (1) of the present invention have high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate or tetrahydrofuran, etc. , it is also possible to form a film by a spin coating method, an inkjet method, a casting method, or an immersion method using a general-purpose apparatus.

Typical structures of the organic electroluminescent device in which the effects of the present invention are obtained include a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.

An anode and a cathode of the organic electroluminescent element are connected to a power supply via an electrical conductor. By applying an electric potential between the anode and the cathode, the organic electroluminescent device operates. Holes are injected into the organic electroluminescent device from the anode, and electrons are injected into the organic electroluminescent device from the cathode.

The organic electroluminescent device is typically coated on a substrate, and an anode or cathode may be in contact with the substrate. The electrode in contact with the substrate is referred to as a lower electrode for convenience. In general, the lower electrode is an anode, but in the organic electroluminescent device of the present invention, it is not limited to such a form. The substrate may be light-transmissive or opaque, depending on the intended direction of light emission. The light-transmitting property is preferable for viewing electroluminescent light emission through the substrate. Transparent glass or plastic is generally employed as such a substrate. The substrate may have a composite structure including multiple material layers.

If the electroluminescent light emission is viewed through the anode, the anode must pass or substantially pass the light emission. A general transparent anode (anode) material used in the present invention is indium-tin oxide (ITO), indium-zinc oxide (IZO) or tin oxide, but other metal oxides such as aluminum or indium-doped type Tin oxide, magnesium-indium oxide, or nickel-tungsten oxide may also help. In addition to these oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide or metal sulfides such as zinc sulfide can be used as the anode. The anode can be modified with plasma-deposited fluorocarbon. For applications in which electroluminescence emission is seen only through the cathode, the transmissive properties of the anode are not critical, and any conductive material, transparent, opaque or reflective, may be used. Examples of conductors for this use include gold, iridium, molybdenum, palladium and platinum.

A hole injection layer may be provided between the anode and the hole transport layer. The hole injection material can help to improve the film-forming properties of a subsequent organic layer, and to facilitate injection of holes into the hole transport layer. As an example of a material suitable for use in the hole injection layer, a porphyrin compound, a plasma deposition type fluorocarbon polymer, and an amine having an aromatic ring such as a biphenyl group and a carbazole group, for example, m-MTDATA(4,4',4 "-tris[(3-methylphenyl)phenylamino]triphenylamine), 2T-NATA(4,4',4"-tris[(N-naphthalen-2-yl)-N-phenylamino]triphenylamine) , triphenylamine, tritolylamine, tolyldiphenylamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, N,N,N'N'-tetrakis(4-methylphenyl)-1,1'-biphenyl-4,4'-diamine, MeO-TPD(N,N,N'N'-tetrakis(4) -Methoxyphenyl)-1,1'-biphenyl-4,4'-diamine), N,N'-diphenyl-N,N'-dinaphthyl-1,1'-biphenyl-4, 4'-diamine, N,N'-bis(methylphenyl)-N,N'-bis(4-normalbutylphenyl)phenanthrene-9,10-diamine or N,N'-diphenyl-N,N '-bis(9-phenylcarbazol-3-yl)-1,1'-biphenyl-4,4'-diamine etc. are mentioned.

The hole transporting layer of the organic electroluminescent device preferably contains at least one hole transporting compound, for example, an aromatic tertiary amine. Aromatic tertiary amine means a compound containing at least one trivalent nitrogen atom, the trivalent nitrogen atom is bonded only to a carbon atom, and at least one of these carbon atoms forms an aromatic ring. Specifically, the aromatic tertiary amine may be an arylamine, such as monoarylamine, diarylamine, triarylamine, or high molecular weight arylamine.

As the hole transport material, an aromatic tertiary amine having at least one amine group can be used. In addition, a polymer hole transport material can be used. For example, poly(N-vinylcarbazole) (PVK), polythiophene, polypyrrole or polyaniline may be used. For example, NPD (N,N'-bis(naphthalen-1-yl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine), α-NPD (N ,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine), TPBi(1,3,5-tris(1-phenyl) -1H-benzimidazol-2-yl)benzene) or TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-dia min) and the like.

Between the hole injection layer and the hole transport layer, as a charge generating layer, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile ( HAT-CN) may be provided.

The light emitting layer of the organic electroluminescent device contains a phosphorescent material or a fluorescent material, and in this case, emits light as a result of recombination of electron-hole pairs in this region. The light emitting layer may consist of a single material containing both a low molecular weight and a polymer, but more generally consists of a host material doped with a guest compound, in this case, light emission mainly occurs from a dopant, and an arbitrary color is emitted. can hold

As a host material of a light emitting layer, the compound which has a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthryl group is mentioned, for example. For example, DPVBi(4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCｚVBi(4,4'-bis(9-ethyl-3-carbazovinylene) ) 1,1'-biphenyl), TBADN (2-tert-butyl-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) or 9,10- Bis(biphenyl)anthracene etc. are mentioned.

The host material in the light emitting layer may be an electron transport material defined below, a hole transport material defined above, or another material that supports hole/electron recombination, or a combination of these materials.

Examples of useful fluorescent dopants include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine and quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium or thiapyrylium. compounds, fluorene derivatives, peripranthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyryl compounds, and the like.

Examples of useful phosphorescent dopants include organometallic complexes of transition metals of iridium, platinum, palladium or osmium.

As an example of a dopant, Alq ₃ (tris(8-hydroxyquinoline)aluminum)), DPAVBi(4,4'-bis[4-(di-para-tolylamino)styryl]biphenyl), perylene, Ir (PPy) ₃ (tris(2-phenylpyridine)iridium(III) or FlrPic(bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III) and the like.

The thin film forming material used for forming the electron transporting layer of the organic electroluminescent device of the present invention is the triazine compound (1) of the present invention. The electron transport layer may contain another electron transport material, and examples of the electron transport material include an alkali metal complex, an alkaline earth metal complex, and an earth metal complex. Preferred alkali metal complexes, alkaline earth metal complexes and earth metal complexes include, for example, 8-hydroxyquinolinatolithium (Liq), bis(8-hydroxyquinolinato)zinc, and bis(8-hydroxyqui Nolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyl) Roxyquinolinato)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-crezolato)gallium, bis(2-methyl-8-quinolinato)-1-naphtolatoaluminum or bis(2-methyl-8 -quinolinato)-2-naphtolatogallium etc. are mentioned.

Between the light emitting layer and the electron transport layer, a hole blocking layer may be formed for the purpose of improving carrier balance. Preferred compounds as the hole blocking layer are BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline) , BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenorato)aluminum) or bis(10-hydroxybenzo[h]quinolinato)beryllium).

In the organic electroluminescent device of the present invention, an electron injection layer may be formed for the purpose of improving electron injection properties and improving device characteristics (eg, luminous efficiency, low voltage driving or high durability).

Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidenemethane, anthraqui. nodimethane or anthrone; and the like. In addition, the above-described metal complexes or alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO _X , AlO _X , SiN _X , SiON, AlON, GeO _X , LiO Inorganic compounds such as various oxides, nitrides, and oxynitrides such as _X , LiON, TiO _X , TiON, TaO _X , TaON, TaN _X , and C can also be used.

When light emission is seen only through the anode, the cathode used in the present invention can be formed of almost any conductive material. Preferred negative electrode 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 ) mixture, indium, lithium/aluminum mixtures, rare earth metals, and the like.

Example

Hereinafter, although this invention is demonstrated in more detail based on an Example, this invention is not limited at all by these Examples and is interpreted.

¹ H-NMR measurement was performed using Gemini200 (made by Varian). The luminescence characteristics of the organic electroluminescent device were evaluated using a luminance meter of LUMINANCEMETER (BM-9) (manufactured by TOPCON) by applying a direct current to the fabricated device at room temperature.

Example-1

Under argon stream, 3-(4,6-diphenylpyridin-2-yl)phenylboronic acid (1.09g, 3.09mmol), 2-(3-bromophenyl)-4,6-diphenyl-1; 3,5-triazine (1.00 g, 2.58 mmol) and tetrakis(triphenylphosphine)palladium (96 mg, 0.077 mmol) were suspended in tetrahydrofuran (50 mL). To this was added a 2M aqueous potassium carbonate solution (4.0 ml, 8.00 mmol), followed by stirring at 75°C for 31 hours. After slow cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 mL), methanol (50 mL), tetrahydrofuran (10 mL) and hexane (50 mL) were added to the obtained slurry, stirred at 75°C, and the precipitated solid was separated by filtration. The obtained solid was washed with water (50 mL), methanol (50 mL), and hexane (50 mL). This solid was dissolved in ethyl acetate (200 ml), filtered through Celite, and the filtrate was concentrated under reduced pressure. After the concentrate was dried and solidified, the obtained solid was purified by recrystallization (ethyl acetate) to obtain the desired 4,6-diphenyl-2-[3'-(4,6-diphenylpyridin-2-yl)-bi A white solid (amount 0.95 g, yield 60%) of phenyl-3-yl]-1,3,5-triazine (Compound A-1) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.57 (m, 12H), 7.63 (dd, J=16,8.0 Hz, 2H), 7.72 (d, J=7.6 Hz, 2H), 7.77 ( d, J=7.7Hz, 1H), 7.88-7.90(m, 2H), 7.94(s, 1H), 8.16-8.21(m, 3H), 8.48(s, 1H), 8.73-8.76(m, 5H) , 9.04(s, 1H).

Example-2

Under argon stream, 2- (2-bromophenyl) -4,6-diphenylpyridine (1.00 g, 2.59 mmol), 2- [3- { (4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl}]-4,6-diphenyl-1,3,5-triazine (1.47 g, 3.38 mmol) and tetrakis(triphenylphosphine)palladium ( 0.121 g, 0.105 mmol) was suspended in tetrahydrofuran (26 mL). To this, a 2M aqueous potassium carbonate solution (3.9 ml, 7.80 mmol) was added, and the mixture was stirred at 75°C for 49 hours. After slow cooling to room temperature, the reaction solution was concentrated under reduced pressure. Methanol (30 mL) and ethyl acetate (5 mL) were added to the obtained concentrate, stirred at 78°C, and the precipitated solid was separated by filtration. The obtained solid was washed with water (30 mL), methanol (30 mL), and hexane (30 mL). This solid was dissolved in ethyl acetate (200 ml), 10 mg of activated carbon was added, filtered through Celite, and the filtrate was concentrated under reduced pressure. Hexane (30 mL) and ethyl acetate (5 mL) were added to the obtained concentrate, stirred at 70°C, and the precipitated solid was separated by filtration. The obtained solid was purified by silica gel column chromatography (chloroform: hexane), and the desired 4,6-diphenyl-2-[2'-(4,6-diphenylpyridin-2-yl)-biphenyl-3 -yl]-1,3,5-triazine (Compound A-421) as a white solid (amount 1.52 g, yield 76%) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24-7.34 (m, 9H), 7.38 (t, J=7.3 Hz, 4H), 7.44-7.54 (m, 6H), 7.58 (m, 1H), 7.64(s, 1H), 7.81(m, 2H), 7.91(m, 1H), 8.61(d, J=8.1Hz, 4H), 8.63-8.66(m, 1H), 8.68(m, 1H).

Example-3

Changed 1.00 g of 3-(4,6-diphenylpyridin-2-yl)phenylboronic acid to 1.26g of 3-[4-(4-dibenzofuryl)-6-phenylpyridin-2-yl]phenylboronic acid 4,6-diphenyl-2-{3'-[4-(4-dibenzofuryl)-6-phenylpyridin-2-yl]-biphenyl-3-yl } A white solid (yield 68%) of -1,3,5-triazine (Compound A-41) was obtained. Tg of the obtained compound was 116 degreeC.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.32 (t, J=7.5Hz, 1H), 7.37-7.58 (m, 12H), 7.64 (t, J=7.9Hz, 2H), 7.74 (d, J=7.6Hz, 1H), 7.79(d, J=7.6Hz, 1H), 7.90(d, J=7.7Hz, 1H), 7.95(d, J=7.5Hz, 1H), 7.99(d, J= 7.6 Hz, 1H), 8.22-8.27 (m, 5H), 8.54 (s, 1H), 8.72-8.76 (m, 5H), 9.05 (s, 1H).

Example-4

Except for changing 1.00 g of 2-(2-bromophenyl)-4,6-diphenylpyridine to 1.23 g of 2-(2-bromophenyl)-4-(4-dibenzofuryl)-6-phenylpyridine In the same manner as in Example-2, 4,6-diphenyl-2-{2'-[4-(4-dibenzofuryl)-6-phenylpyridin-2-yl]-biphenyl-3-yl}- A white solid (yield 72%) of 1,3,5-triazine (Compound A-461) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.21-7.36 (m, 11H), 7.42-7.47 (m, 4H), 7.50-7.56 (m, 3H), 7.59-7.63 (m, 2H), 7.81 -7.85(m, 4H), 7.91-7.96(m, 1H), 8.06(s, 1H), 8.59(d, J=6.8Hz, 4H), 8.63(d, J=7.8Hz, 1H), 8.74( s, 1H).

Example-5

Except for changing 1.00 g of 2-(2-bromophenyl)-4,6-diphenylpyridine to 1.23 g of 2-(2-bromophenyl)-4-(2-dibenzofuryl)-6-phenylpyridine In the same manner as in Example-2, 4,6-diphenyl-2-{2'-[4-(2-dibenzofuryl)-6-phenylpyridin-2-yl]-biphenyl-3-yl}- A white solid (yield 53%) of 1,3,5-triazine (Compound A-467) was obtained.

¹ H-NMR (CDCl ₃ ) δ(ppm): 7.04 (t, J=7.6Hz, 1H), 7.28-7.63(m, 20H), 7.72(s, 1H), 7.76(d, J=7.8Hz, 1H), 7.93 (d, J=6.2 Hz, 2H), 7.99-8.03 (m, 1H), 8.63 (d, J=6.9 Hz, 4H), 8.77-8.80 (m, 2H).

Example-6

Under a nitrogen stream, 4- (2-bromophenyl) -2- (4-biphenyl) -6-phenylpyridine (3.0 g, 6.49 mmol), 2- [3- { (4,4,5,5) -tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}]-4,6-diphenyl-1,3,5-triazine (3.00 g, 6.49 mmol), palladium acetate (29.1) mg, 0.130 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (124 mg, 0.260 mmol) were suspended in toluene (50 mL). To this was added a 4.0 M aqueous sodium hydroxide solution (4.87 ml, 19.5 mmol), followed by stirring at 100°C for 4 hours. After slow cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (30 ml) and methanol (60 ml) were added to the obtained concentrate, and the precipitated solid was separated by filtration. The obtained solid was purified by silica gel column chromatography (chloroform/hexane) to obtain the desired 2-{2'-[2-(4-biphenyl)-6-phenylpyridin-4-yl]-biphenyl-3- One}-4,6-diphenyl-1,3,5-triazine (Compound A-754) was obtained as a white solid (amount 4.14 g, yield 92%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.68 (m, 24H), 7.96 (d, J=7.8 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 8.69 (d, J=7.2 Hz, 5H), 8.78 (s, 1H).

Example-7

Under nitrogen stream, 4- (3-bromophenyl) -2- (4-biphenyl) -6-phenylpyridine (3.0 g, 6.49 mmol), 2- [3- { (4,4,5,5) -tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}]-4,6-diphenyl-1,3,5-triazine (3.00 g, 6.49 mmol), palladium acetate (29.1) mg, 0.130 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (124 mg, 0.260 mmol) were suspended in toluene (50 mL). A 4.0 M aqueous sodium hydroxide solution (4.87 ml, 19.5 mmol) was added thereto, and the mixture was stirred at 100°C for 2 hours. After slow cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (30 ml) and methanol (60 ml) were added to the obtained concentrate, and the precipitated solid was separated by filtration. The obtained solid was purified by silica gel column chromatography (chloroform/hexane) to obtain the desired 2-{3'-[2-(4-biphenyl)-6-phenylpyridin-4-yl]-biphenyl-3- One}-4,6-diphenyl-1,3,5-triazine (Compound A-334) was obtained as a white solid (amount 3.87 g, yield 86%).

Tg of the obtained compound was 107 degreeC.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39 (d, J=7.2 Hz, 1H), 7.46-7.62 (m, 11H), 7.67-7.77 (m, 6H), 7.83 (d, J=8.1 Hz, 1H), 7.87(d, J=7.8Hz, 1H), 7.93(d, J=7.5Hz, 1H), 8.01(s, 1H), 8.05(s, 1H), 8.11(s, 1H), 8.26(d, J=8.1Hz, 2H), 8.33(d, J=7.8Hz, 2H), 8.79-8.85(m, 5H), 9.09(s, 1H).

Example-8

1.00 g of 2-(2-bromophenyl)-4,6-diphenylpyridine to 1.26 g of 2-(3-bromophenyl)-4-(1-naphthyl)-6-(2-naphthyl)pyridine 4,6-diphenyl-2-{3'-[4-(1-naphthyl)-6-(2-naphthyl)pyridin-2-yl]- A white solid (yield 47%) of biphenyl-3-yl}-1,3,5-triazine (Compound A-7) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.55 (m, 12H), 7.64 (dd, J=7.4 Hz, 2H), 7.80 (d, J=7.3 Hz, 2H), 7.87-7.96 ( m, 7H), 7.99(s, 1H), 8.24(d, J=8.0Hz, 1H), 8.37(d, J=8.4Hz, 1H), 8.51(s, 1H), 8.61(s, 1H), 8.71-8.74 (m, 5H), 9.04 (s, 1H).

Synthesis Example-1

1.00 g of 3-(4,6-diphenylpyridin-2-yl)phenylboronic acid was changed to 1.09g of 3-[4-(3-chlorophenyl)-6-phenylpyridin-2-yl]phenylboronic acid 4,6-diphenyl-2-{3'-[4-(3-chlorophenyl)-6-phenylpyridin-2-yl]-biphenyl-3-yl}- A white solid of 1,3,5-triazine (yield 77%) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.66 (m, 14H), 7.69 (m, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.83 (s, 1H), 7.87- 7.90(m, 2H), 8.15-8.20(m, 3H), 8.47(s, 1H), 8.72-8.76(m, 5H), 9.02(s, 1H).

Example-9

Under argon stream, 4,6-diphenyl-2-{3'-[4-(3-chlorophenyl)-6-phenylpyridin-2-yl]-biphenyl-3-yl}-1,3,5 -Triazine (1.00g, 1.54mmol), 3-pyridine boronic acid (0.52g, 4.23mmol), palladium acetate (14.8mg, 0.066mmol) and 2-dicyclohexylhospino-2',4' ,6'-triisopropylbiphenyl (61.8 mg, 0.130 mmol) was suspended in tetrahydrofuran (70 mL), and stirred at 75° C. for 48 hours. After slow cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 ml) and methanol (10 ml) were added to the resulting slurry, and the precipitated solid was filtered off, and washed with water (30 ml), methanol (30 ml) and hexane (30 ml). The obtained solid was purified by silica gel column chromatography (chloroform), and the desired 4,6-diphenyl-2-(3'-{4-[3-(3-pyridyl)phenyl]-6-phenylpyridine- 2-yl}-biphenyl-3-yl)-1,3,5-triazine (Compound A-96) was obtained as a white solid (amount 0.90 g, yield 84%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.62 (m, 14H), 7.74 (t, J=6.2 Hz, 2H), 7.85-7.92 (m, 5H), 8.17 (d, J=7.7) Hz, 3H), 8.47(s, 1H), 8.56(d, J=4.2Hz, 1H), 8.70(d, J=7.5Hz, 5H), 8.86(s, 1H), 9.00(s, 1H).

Example-10

In the same manner as in Example 9, except that 1.00 g of 3-pyridine boronic acid was changed to 1.00 g of 4-pyridine boronic acid, 4,6-diphenyl-2-(3'-{4-[3-(4-pyri A white solid (yield 23%) of dil)phenyl]-6-phenylpyridin-2-yl}-biphenyl-3-yl)-1,3,5-triazine (Compound A-932) was obtained.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.36-7.54 (m, 9H), 7.62 (t, J=7.9 Hz, 2H), 7.70 (t, J=7.5 Hz, 1H), 7.76 (d, J=7.8Hz, 2H), 7.85(m, 2H), 7.90-7.94(m, 2H), 7.99-8.08(m, 3H), 8.17(t, J=8.4Hz, 3H), 8.44(s, 1H) ), 8.68-8.74 (m, 7H), 8.99 (s, 1H).

4,6-diphenyl-2-[4'-(4,6-diphenylpyridin-2-yl)-biphenyl-3-yl]-1,3,5-triazine described in U2016/002864 Compared with (ETL-3, compound A-721 of patent document 2), it turns out that the cyclic azine compound of this invention has a high triplet excitation level.

Next, device evaluation will be described.

Structural formulas of the compounds used for device evaluation and their abbreviations are shown below.

Device Example 1

As the substrate, a glass substrate with an ITO transparent electrode in which indium-tin oxide (ITO) (film thickness 110 nm) having a width of 2 mm was patterned in a stripe shape was used. After washing this board|substrate with isopropyl alcohol, it surface-treated by ozone ultraviolet washing. On the substrate after washing, vacuum deposition of each layer was performed by a vacuum deposition method, and an organic electroluminescent device having a light emitting area of 4 mm 2 as shown in the cross-sectional view in FIG. 1 was produced. In addition, each organic material was formed into a film by the resistance heating method.

First, the glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa.

Thereafter, on the glass substrate with the ITO transparent electrode shown in Fig. 1 (1), as an organic compound layer, the hole injection layer 2, the charge generation layer 3, the hole transport layer 4, the light emitting layer 5, and the electron transport layer (6) and the cathode layer (7) were both deposited by vacuum deposition while laminating in this order.

As the hole injection layer 2, sublimation-refined HIL was formed into a film at a rate of 0.15 nm/sec at 65 nm.

As the charge generating layer 3, 5 nm of sublimation-refined HAT was formed into a film at a rate of 0.05 nm/sec.

As the hole transport layer 4, 10 nm of HTL was formed into a film at a rate of 0.15 nm/sec.

As the light emitting layer 5, 25 nm of EML-1 and EML-2 were deposited at a ratio of 95:5 (film formation rate of 0.18 nm/sec).

As the electron transport layer 6, 4,6-diphenyl-2-[3'-(4,6-diphenylpyridin-2-yl)-biphenyl-3-yl]-1 synthesized in Example-1 ,3,5-triazine (Compound A-1) and Liq were deposited at a ratio of 50:50 (weight ratio) at 30 nm (film formation rate of 0.15 nm/sec).

Finally, the metal mask was arranged so as to be perpendicular to the ITO stripe, and the cathode layer 7 was formed. The cathode layer 7 is formed by depositing silver/magnesium (1/10 by weight) and silver at 80 nm (film-forming rate: 0.5 nm/sec) and 20 nm (film-forming rate: 0.2 nm/sec), respectively, in this order, It was set as the two-layer structure.

Each film thickness was measured with a stylus type film thickness meter (DEKTAK).

In addition, this device was sealed in a nitrogen atmosphere glove box with oxygen and moisture concentration of 1 ppm or less. For sealing, the glass sealing cap and the said film-forming board|substrate epoxy type|mold ultraviolet curing resin (made by Nagase Chemtex) were used.

A direct current was applied to the organic electroluminescent device fabricated as described above, and luminescence characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON Corporation. As the luminescence characteristics, the voltage (V) and the current efficiency (cd/A) when a current density of 10 mA/cm 2 was applied were measured, and the device lifetime (h) at the time of continuous lighting was measured. In addition, the device lifetime (h) in Table 2 is measured when the luminance decay time during continuous lighting when the fabricated device is driven at an initial luminance of 800 cd/m 2 , and when the luminance (cd/m 2 ) decreases by 10% The time taken until The device lifetime was expressed as a relative value with the device lifetime h in the device reference example 1 described above as a reference value (100). A result is shown in Table 2.

Device Example 2

In Device Example 1, 4,6-diphenyl-2-[2'-(4,6-diphenylpyridin-2-yl)-biphenyl- synthesized in Example-2 instead of Compound A-1 3-yl]-1,3,5-triazine (Compound A-421) was produced and evaluated in the same manner as in Device Example 1, except for using an organic electroluminescent device. A result is shown in Table 2. In addition, about the element lifetime, after measuring the element lifetime (h), it was shown as the relative value which made the element lifetime of the element reference example 1 100.

Device Reference Example 1

In Device Example 1, 2-[5-(9-phenanthryl)-4'-(2-pyrimidyl)biphenyl- described in Japanese Patent Application Laid-Open No. 2011-063584 instead of Compound A-2 3-yl]-4,6-diphenyl-1,3,5-triazine (ETL-1), except for using an organic electroluminescent device was manufactured and evaluated in the same manner as in Device Example 1. The results are shown in Table 2. In addition, about the element lifetime, after measuring the element lifetime (h), the element lifetime of this element reference example 1 was made into the reference value (100).

Device Example 3

As the substrate, a glass substrate with an ITO transparent electrode in which indium-tin oxide (ITO) (film thickness 110 nm) having a width of 2 mm was patterned in a stripe shape was used. After washing this board|substrate with isopropyl alcohol, it surface-treated by ozone ultraviolet washing. On the substrate after washing, vacuum deposition of each layer was performed by a vacuum deposition method to prepare an organic electroluminescent device having a light emission area of 4 mm 2 . In addition, each organic material was formed into a film by the resistance heating method.

First, the glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa.

Then, on the glass substrate with the ITO transparent electrode, as an organic compound layer, a hole injection layer, a charge generation layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a first electron transport layer, a second electron transport layer and a cathode layer, While laminating in order, all were formed into a film by vacuum deposition.

As a hole injection layer, 55 nm of sublimation-refined HIL was formed into a film at the speed|rate of 0.15 nm/sec.

As the charge generating layer, 5 nm of sublimation-refined HAT was formed at a rate of 0.05 nm/sec.

As the first hole transport layer, 10 nm of HTL was deposited at a rate of 0.15 nm/sec.

As the second hole transport layer, 10 nm of HTL-2 was formed at a rate of 0.15 nm/sec.

As the light emitting layer, 25 nm of EML-3 and EML-4 were formed in a ratio of 95:5 (film formation rate of 0.18 nm/sec).

As the first electron transport layer, 5 nm of ETL-2 was formed at a rate of 0.15 nm/sec.

As the second electron transport layer, 4,6-diphenyl-2-{3'-[4-(4-dibenzofuryl)-6-phenylpyridin-2-yl]-biphenyl- synthesized in Example-3 3-day} -1,3,5-triazine (Compound A-41) and Liq were deposited at 25 nm in a ratio of 50:50 (weight ratio) (film formation rate of 0.15 nm/sec).

Finally, the metal mask was arranged so as to be perpendicular to the ITO stripe, and the cathode layer 19 was formed into a film.

The cathode layer is formed by depositing silver/magnesium (1/10 by weight) and silver in this order, respectively, at 80 nm (film-forming rate: 0.5 nm/sec) and 20 nm (film-forming rate: 0.2 nm/sec), and has a two-layer structure. was done with

Each film thickness was measured with a stylus type film thickness meter (DEKTAK).

In addition, this device was sealed in a glove box in a nitrogen atmosphere with oxygen and moisture concentration of 1 ppm or less. For sealing, the glass sealing cap and the said film-forming board|substrate epoxy type|mold ultraviolet curing resin (made by Nagase Chemtex) were used.

A direct current was applied to the organic electroluminescent device fabricated as described above, and luminescence characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by Topcon. As the luminescence characteristics, the voltage (V) and the current efficiency (cd/A) when a current density of 10 mA/cm 2 was applied were measured, and the device lifetime (h) at the time of continuous lighting was measured. In addition, the device lifetime (h) in Table 1 is measured by measuring the luminance decay time during continuous lighting when the fabricated device is driven with an initial luminance of 1000 cd/m2, and when the luminance (cd/m2) decreases by 10% The time taken until Voltage, current efficiency, and device lifetime are expressed as relative values with the result in Device Reference Example 2 described later as a reference value (100). A result is shown in Table 3.

Device Example 4

In Device Example 3, 4,6-diphenyl-2-[2'-(4,6-diphenylpyridin-2-yl)-biphenyl- synthesized in Example-2 instead of compound A-41 3-yl]-1,3,5-triazine (Compound A-421) was produced and evaluated in the same manner as in Device Example 3, except for using an organic electroluminescent device. A result is shown in Table 3. In addition, about the element lifetime, after measuring the element lifetime (h), the element lifetime of the element reference example 2 was shown as the relative value which made 100.

Device Reference Example 2

In Device Example 3, 2-[5-(9-phenanthryl)-4'-(2-pyrimidyl)biphenyl- described in Japanese Patent Application Laid-Open No. 2011-063584 instead of Compound A-41 3-yl]-4,6-diphenyl-1,3,5-triazine (ETL-1), except for using an organic electroluminescent device in the same manner as in Device Example 3 was manufactured and evaluated. The results are shown in Table 3. In addition, about the element lifetime, after measuring the element lifetime (h), the element lifetime of this element reference example 2 was made into the reference value (100).

Although this invention was demonstrated with reference to the specific embodiment in detail, it is clear for those skilled in the art that various changes and correction can be added without deviating from the essence and range of this invention.

In addition, the specification of Japanese Patent Application No. 2016-126040 for which it applied on June 24, 2016, a claim, drawing, and the abstract are all cited in this specification, and it takes in as an indication of the specification of this invention .

The triazine compound (1) of the present invention is excellent in film quality heat resistance, and by using the compound, an organic electroluminescent device having excellent long lifespan and luminous efficiency can be provided.

Moreover, the triazine compound (1) of this invention is used as an electron transport material for organic electroluminescent elements excellent in a low drive voltage. In addition, according to the present invention, it is possible to provide an organic electroluminescent device having excellent power consumption.

Further, since the triazine compound of the present invention has good thermal stability during sublimation purification, it is excellent in operability of sublimation purification, and it is possible to provide a material with few impurities that cause device deterioration of organic electroluminescent devices. In addition, since the triazine compound of the present invention has excellent stability of the deposited film, it is possible to provide an organic electroluminescent device having a long lifespan.

In addition, the thin film made of the triazine compound (1) of the present invention has excellent electron transport ability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics, etc., so it is useful as a material for an organic electroluminescent device and , an electron transport material, a hole block material, a light emitting host material, and the like. It is particularly useful when used as an electron transport material. In addition, since the triazine compound (1) of the present invention is a broadband gap compound, it can be suitably used not only for conventional fluorescent devices but also for phosphorescent devices.

Claims (13)

A triazine compound represented by the general formula (1):

(in general formula (1),
Ar ¹ represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group), and two Ar ¹ are the same.
Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms (the group represented by (a) is a phenyl group, a tolyl group, a pyridyl group, and a methyl group may have a pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
Ar ⁴ and Ar ⁷ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or (c) ) a monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of H, C, O and S (the group represented by (a), (b) and (c) above is a fluorine atom, may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).
The total number of ring-constituting carbon atoms of Ar ² , Ar ³ and Ar ⁴ and the total number of ring-constituting carbon atoms of Ar ⁵ , Ar ⁶ and Ar ⁷ are 5 to 25 in either case.
A represents a single bond.
B ¹ and B ² represent a single bond or a hydrogen atom. However, either one of B ¹ or B ² represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, either Z ¹ or Z ² represents a nitrogen atom, and the other represents CH.)
However, the triazine compound excludes compound A-1 represented by the following formula:

The triazine compound according to claim 1, wherein Ar ¹ represents a phenyl group, a tolyl group, a naphthyl group or a biphenyl group, and two Ar ¹ are the same. The triazine compound according to claim 1, wherein Ar ¹ are all phenyl groups.
The method according to claim 1, wherein Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, and a perylene group. a diyl group, a fluoranthenyl group, a triphenylenyl group (these groups may have a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms); or a single bond;
and Ar ⁴ and Ar ⁷ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluoranthenyl group, a triphenylenyl group , triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group or dibenzothienyl group (these groups are fluorine atom, A triazine compound characterized in that it may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms). The method according to claim 1, wherein Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, and a perylene group. a diyl, a fluoranthenyl group, a triphenylenyl group (these groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond;
and Ar ⁴ and Ar ⁷ are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group, a peryleneyl group, a fluoranthenyl group, a triphenylenyl group , triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group or dibenzothienyl group (these groups are fluorine atom, A triazine compound characterized in that it may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms). The group according to claim 1, wherein the group represented by -Ar ² -Ar ³ -Ar ⁴ and the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, and a phenanthrylphenyl group. , fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothien A ylphenyl group, a pyridyldibenzofurylphenyl group, a bipyridyl group, a naphthyl group, a benzothienyl group, a benzofuryl group, a phenanthryl group, an anthryl group, a dibenzothienyl group or a dibenzofuryl group (these groups include a fluorine atom, Or it may be substituted with a methyl group), characterized in that the triazine compound. The group according to claim 1, wherein the group represented by -Ar ² -Ar ³ -Ar ⁴ and the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, and a phenanthrylphenyl group. , pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group or a dibenzofuryl group (these groups may be substituted with a methyl group), the triazine compound. The method according to claim 1, wherein any one of the group represented by -Ar ² -Ar ³ -Ar ⁴ or the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, A pyridylphenyl group, a pyrimidylphenyl group, a dibenzothienylphenyl group, a dibenzofurylphenyl group, a pyridyldibenzothienylphenyl group, a pyridyldibenzofurylphenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or triazine, which is a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group) and the other is a phenyl group, a biphenyl group, a pyridyl group or a naphthyl group (these groups may be substituted with a methyl group) compound. The method according to claim 1, wherein any one of the group represented by -Ar ² -Ar ³ -Ar ⁴ or the group represented by -Ar ⁵ -Ar ⁶ -Ar ⁷ is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, A pyridylphenyl group, a pyrimidylphenyl group, a dibenzothienylphenyl group, a dibenzofurylphenyl group, a pyridyldibenzothienylphenyl group, a pyridyldibenzofurylphenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or It is a dibenzofuryl group (these groups may be substituted by the methyl group), The triazine compound whose other is a phenyl group or a naphthyl group. A method for producing a triazine compound represented by the general formula (1) according to claim 1, characterized by using a coupling reaction:

(in general formula (1),
Ar ¹ represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group), and two Ar ¹ are the same.
Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms (the group represented by (a) is a phenyl group, a tolyl group, a pyridyl group, and a methyl group may have a pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
Ar ⁴ and Ar ⁷ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or (c) ) a monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of H, C, O and S (the group represented by (a), (b) and (c) above is a fluorine atom, may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).
The total number of ring-constituting carbon atoms of Ar ² , Ar ³ and Ar ⁴ and the total number of ring-constituting carbon atoms of Ar ⁵ , Ar ⁶ and Ar ⁷ are 5 to 25 in either case.
A represents a single bond.
B ¹ and B ² represent a single bond or a hydrogen atom. However, either one of B ¹ or B ² represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, either Z ¹ or Z ² represents a nitrogen atom, and the other represents CH.)
However, the triazine compound excludes compound A-1 represented by the following formula:

A material for an organic electroluminescent device comprising the triazine compound represented by the general formula (1) according to claim 1 :

(in general formula (1),
Ar ¹ represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group), and two Ar ¹ are the same.
Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms (the group represented by (a) is a phenyl group, a tolyl group, a pyridyl group, and a methyl group may have a pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
Ar ⁴ and Ar ⁷ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or (c) ) a monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of H, C, O and S (the group represented by (a), (b) and (c) above is a fluorine atom, may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).
The total number of ring-constituting carbon atoms of Ar ² , Ar ³ , and Ar ⁴ and the total number of ring-constituting carbon atoms of Ar ⁵ , Ar ⁶ and Ar ⁷ are 5 to 25 in either case.
A represents a single bond.
B ¹ and B ² represent a single bond or a hydrogen atom. However, either one of B ¹ or B ² represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, either Z ¹ or Z ² represents a nitrogen atom, and the other represents CH.)
However, the triazine compound excludes compound A-1 represented by the following formula:

An electron transporting material for an organic electroluminescent device comprising a triazine compound represented by the general formula (1) according to claim 1 :

(in general formula (1),
Ar ¹ represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group or a phenyl group), and two Ar ¹ are the same.
Ar ² , Ar ³ , Ar ⁵ and Ar ⁶ are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms (the group represented by (a) is a phenyl group, a tolyl group, a pyridyl group, and a methyl group may have a pyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
Ar ⁴ and Ar ⁷ are each independently, (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or (c) ) a monocyclic or condensed cyclic heteroaromatic group having 3 to 25 carbon atoms consisting of an atom selected from the group consisting of H, C, O and S (the group represented by (a), (b) and (c) above is a fluorine atom, may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).
The total number of ring-constituting carbon atoms of Ar ² , Ar ³ and Ar ⁴ and the total number of ring-constituting carbon atoms of Ar ⁵ , Ar ⁶ and Ar ⁷ are 5 to 25 in either case.
A represents a single bond.
B ¹ and B ² represent a single bond or a hydrogen atom. However, either one of B ¹ or B ² represents a single bond and forms a single bond with A, and the other represents a hydrogen atom.
Z ¹ and Z ² each independently represent a nitrogen atom or CH. However, either Z ¹ or Z ² represents a nitrogen atom, and the other represents CH).
However, the triazine compound excludes compound A-1 represented by the following formula:

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