WO2015182769A1 - Quinazoline and benzoquinazoline compounds and production and use of same - Google Patents

Abstract

Provided are compounds shown by general formula (1) as an organic electroluminescent device having high efficiency, low voltage driving, and long life and a material making this possible, especially an electron transport material, methods for producing these compounds, and an organic electroluminescent device using these compounds. (In the formula, Ar1 and Ar2 are as described in the specification, A represents general formula (2-1), general formula (2-2), or general formula (2-3). In general formula (2-1), general formula (2-2), and general formula (2-3), ＊ represents a linking site, Ar3-Ar7, R11-R16, R21-R26, R31, and R32 are as described in the specification.)

Description

Quinazoline and benzoquinazoline compounds, their production and use

The present invention relates to a quinazoline and a benzoquinazoline compound for providing a high-efficiency organic electroluminescence device excellent in drivability and light emission characteristics represented by the general formula (1), and a method for producing the same.

The organic electroluminescent element has a structure in which a light emitting layer containing a light emitting material is sandwiched between a hole transport layer and an electron transport layer, and an anode and a cathode are attached to the outside, and holes injected into the light emitting layer and It is a self-emitting element that utilizes a light emission phenomenon (fluorescence or phosphorescence) when excitons generated by electron recombination are deactivated. Since it is a self-luminous type, it is excellent in visibility, and since it is a completely solid element, it is easy to handle and manufacture. In addition, since it is a thin film type device, it is attracting attention from the viewpoints of space saving and portability, and is applied to displays, lighting, and the like. At present, the organic electroluminescence device has begun to be used for commercial purposes. However, further improvement in light emission efficiency, reduction in driving voltage, and longer life are required for energy saving.

In order to make the organic electroluminescence device highly efficient, low voltage drive, and long life, it is necessary to efficiently inject and transport holes and electrons to the light emitting layer and recombine them. In this regard, improvement of each material constituting the organic electroluminescent element, particularly an electron transporting material, has been demanded.

Patent Document 1 discloses an electron transport layer host material capable of obtaining an organic EL element having a long emission lifetime and a low driving voltage, and an element using the same. However, in order to use this material for an organic electroluminescent device, a doped material is indispensable. When used as a single electron transport layer that does not contain a doped material, the device has a higher driving voltage or significantly reduced efficiency, so that improvement can be achieved. It was sought after.

Patent Document 2 discloses an electron transport material for providing an organic electroluminescent device having high luminous efficiency. An organic electroluminescent device using a benzoquinazoline compound disclosed in the above document is a benzoquinazoline. There was a problem that it was difficult to lower the driving voltage due to the influence of the substituent at the 2-position.

WO2006 / 104118 WO2013 / 180376

Organic electroluminescent elements are used in various display elements, but more efficient light emission is required particularly for practical use of large displays and lighting. An object of the present invention is to provide an electron transporting material which is excellent in the lifetime characteristics of the device and excellent in the light emitting efficiency of the device as compared with a conventionally known electron transporting material for an organic electroluminescence device.

As a result of intensive studies to solve the above problems, the present inventors have found that an organic electroluminescent device using a quinazoline and benzoquinazoline compound represented by the following general formula (1) as an electron transport layer is a conventionally known material. As compared with the organic electroluminescent device using the ED for the electron transport layer, the inventors have found that the driving voltage is low, the luminous efficiency is improved, and the life is long, and the present invention has been completed.

(In the formula, Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a benzene ring and / or pyridine) Aromatic groups consisting only of 6 to 6 rings in which 2 to 6 rings are connected and / or condensed {These groups include a methyl group, a methoxy group, a fluorine atom, a pyrimidyl group (the pyrimidyl group is a methyl group, a carbon number 2-10 alkyl groups and at least one substituent selected from the group consisting of C6-C18 aromatic hydrocarbon groups), or a C2-C10 alkyl group, alkoxy A group, an alkoxyalkyl group, an ester group or an esteralkyl which may be substituted}.
A represents the general formula (2-1), the general formula (2-2), or the general formula (2-3).

Of the formulas (2-1), (2-2), and (2-3),
* Represents a linking site.
Ar ³ , Ar ⁴ and Ar ⁵ are each an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom, alkyl group having 2 to 10 carbon atoms, alkoxy group, And may be substituted with an alkoxyalkyl group, an ester group or an ester alkyl group).
Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a methyl group, a methoxy group, a fluorine atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom) Or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group.
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ , and R ³² are each independently a hydrogen atom Represents a methyl group, a methoxy group, a phenyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group.
In addition, each hydrogen atom in the formula may independently be a deuterium atom. )
That is, the present invention resides in the following [1] to [20].
[1]
Compound represented by the above general formula (1).
[2]
Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 6 benzene rings and / or pyridine rings. An aromatic group consisting of only six linked and / or condensed six-membered rings {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, Or a pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group). The compound according to [1], which may be substituted}.
[3]
Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 5 benzene rings and / or pyridine rings. An aromatic group consisting of only six linked and / or condensed six-membered rings {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, Or a pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group). The compound according to [1], which may be substituted.
[4]
Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 4 benzene rings and / or pyridine rings. An aromatic group consisting of only six linked and / or condensed six-membered rings {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, Or a pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group). The compound according to [1], which may be substituted}.
[5]
Ar ³ , Ar ⁴ and Ar ⁵ are aromatic hydrocarbon groups having 6 to 12 carbon atoms (the group is a methyl group, a methoxy group, an alkyl group or alkoxy group having 2 to 10 carbon atoms, a pyridyl group, a pyrimidyl group, or The compound according to [1], which may be substituted with a fluorine atom.
[6]
Ar ³ , Ar ⁴ and Ar ⁵ are a phenyl group, a naphthyl group, or a biphenyl group (these groups are a methyl group, a methoxy group, a pyridyl group, a pyrimidyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group) A group, an alkoxyalkyl group, an ester group or an esteralkyl group, which may be substituted).
[7]
The compound according to [1], wherein Ar ³ , Ar ⁴ and Ar ⁵ are a phenyl group, a naphthyl group, or a biphenyl group.
[8]
The compound according to [1], wherein Ar ³ , Ar ⁴ and Ar ⁵ are phenyl groups.
[9]
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ , and R ³² are hydrogen atoms [1 ] The compound of description.
[10]
Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a methyl group, a methoxy group, a fluorine atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms (the group is a methyl group, methoxy group, 2 to The compound according to [1], which may be substituted with a 10 alkyl group, an alkoxy group having 2 to 10 carbon atoms, a pyridyl group, a pyrimidyl group, or a fluorine atom.
[11]
Ar ⁶ and Ar ⁷ are each independently a phenyl group, a naphthyl group, or a biphenyl group (these substituents are a methyl group, a methoxy group, a pyridyl group, a pyrimidyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms) , An alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group), a hydrogen atom, a methyl group, a methoxy group, or a fluorine atom.
[12]
The compound according to [1], wherein Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a phenyl group, a naphthyl group, or a biphenyl group.
[13]
The compound according to [1], wherein Ar ⁶ and Ar ⁷ are each independently a hydrogen atom or a phenyl group.
[14]
In the presence of a metal catalyst, or in the presence of a metal catalyst and a base, a compound represented by general formula (3) described later, a compound represented by general formula (4) described later, and a general formula (5) described below. The method for producing a compound according to [1], wherein the compound is subjected to a coupling reaction in one or two steps.
[15]
The compound according to [14], which is represented by a general formula (3-1) described later, a general formula (3-2) described later, or a general formula (3-3) described later.
[16]
In the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base and in the presence or absence of a nitrogen source, the following general formula (6 -1) and a compound represented by the following general formula (7-1) are subjected to a cyclization reaction, or a compound represented by the following general formula (6-2) and a general formula (described later) The compound represented by 7-2) is subjected to a cyclization reaction, or the compound represented by the general formula (6-3) described later and a compound represented by the general formula (7-3) described later are cyclized. A process for producing a compound represented by the general formula (3-1), the general formula (3-2), or the general formula (3-3) according to [15].
[17]
A compound represented by the following general formula (9-1) or general formula (9-2) described below is present in the presence of an oxidizing agent in the presence or absence of an acid, or in the presence of a base or The method for producing a benzoquinazoline compound represented by the general formula (3-1) or the general formula (3-2) according to [15], wherein the reaction is performed in the absence.
[18]
The material for organic electroluminescent elements containing the compound as described in [1].
[19]
A light emitting layer host material, an electron injection material or an electron transport material comprising the compound according to [1].
[20]
An electron injection material or an electron transport material comprising the compound according to [1].

Since the compound (1) of the present invention has good charge injection and transport properties, it is useful as a material for fluorescent or phosphorescent organic electroluminescence devices, and can be used as an electron transport material and a host material, among others. The organic electroluminescent device having an electron transport layer containing the compound (1) of the present invention is superior in organic EL device using a general-purpose electron transport material, has a low driving voltage, excellent luminous efficiency, and has a long lifetime. .

The band gap of the compound (1) of the present invention is 3.0 eV or more, and the energy of each of the three primary colors (red: 1.9 eV, green: 2.4 eV, blue: 2.8 eV) constituting the panel is obtained. It is a material with a wide band gap sufficient to confine. Therefore, it can be applied to various elements such as a single color display element, a three primary color display element, and a white element for illumination use. Since the compound (1) of the present invention has a high triplet energy, it can be sufficiently applied to phosphorescence. Furthermore, since the solubility can be controlled by changing the substituent, it can be applied not only to a vapor deposition element but also to a coating element.

FIG. 3 is a schematic cross-sectional view of an organic electroluminescent element produced in Test Example-1.

Hereinafter, the present invention (compound (1), its production method, production intermediate used in the production method, use of the production intermediate and compound (1)) will be described in detail.

General formula (1) will be described.

Ar ¹ and Ar ² each independently represent a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 6 benzene rings and / or pyridine rings. Aromatic groups consisting only of six-membered rings that are linked and / or condensed {these groups are methyl, methoxy, fluorine, pyrimidyl (the pyrimidyl is methyl, alkyl of 2 to 10 carbon atoms) And may have at least one substituent selected from the group consisting of an aromatic hydrocarbon group having 6 to 18 carbon atoms), or an alkyl group, alkoxy group, alkoxyalkyl group having 2 to 10 carbon atoms , Optionally substituted with an ester group or an ester alkyl}.

The pyridyl group is not particularly limited, and examples thereof include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.

The pyrimidyl group is not particularly limited, and examples thereof include a 2-pyrimidyl group, a 4-pyrimidyl group, and a 5-pyrimidyl group.

The pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms is not particularly limited, and examples thereof include a 4-phenylpyrimidin-2-yl group, a 5-phenylpyrimidin-2-yl group, 2-phenylpyrimidin-4-yl group, 6-phenylpyrimidin-4-yl group, 2-phenylpyrimidin-5-yl group, 4,6-diphenylpyrimidin-2-yl group, 4-naphthylpyrimidin-2-yl group Group, 5-naphthylpyrimidin-2-yl group, 2-naphthylpyrimidin-4-yl group, 6-naphthylpyrimidin-4-yl group, 2-naphthylpyrimidin-5-yl group, 6-naphthyl-4-phenylpyrimidine -2-yl group, 4-anthracylpyrimidin-2-yl group, 5-anthracylpyrimidin-2-yl group, 2-anthracylpyrimidine-4 Yl group, 6-anthracylpyrimidin-4-yl group, 2-anthracylpyrimidin-5-yl group, 4-phenanthrylpyrimidin-2-yl group, 5-phenanthrylpyrimidin-2-yl group, 2 -Phenanthrylpyrimidin-4-yl group, 6-phenanthrylpyrimidin-4-yl group, 2-phenanthrylpyrimidin-5-yl group, 4-pyrenylpyrimidin-2-yl group, 5-pyrenyl Examples include a pyrimidin-2-yl group, a 2-pyrenylpyrimidin-4-yl group, a 6-pyrenylpyrimidin-4-yl group, and a 2-pyrenylpyrimidin-5-yl group.

Among these, a pyrimidyl group substituted with a phenyl group, a biphenyl group, or a condensed aromatic hydrocarbon group having 10 to 18 carbon atoms consisting of only a 6-membered ring, in terms of good performance as an organic electroluminescent element material. The substituent is not particularly limited, and for example, a pyrimidyl group substituted with a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, or a pyrenyl group is more preferable.

The preferred substituents include 5-phenylpyrimidin-2-yl group, 4,6-diphenylpyrimidin-2-yl group, 5-naphthylpyrimidin-2-yl group, and 4,6-dinaphthylpyrimidin-2-yl. More preferably a group, a 5-phenanthrylpyrimidin-2-yl group, a 5-anthracylpyrimidin-2-yl group, and a 5-pyrenylpyrimidin-2-yl group.

Of these substituents, a 5-phenylpyrimidin-2-yl group, a 4,6-diphenylpyrimidin-2-yl group, and a 4,6-dinaphthylpyrimidin-2-yl group are more preferable.

The aromatic group consisting of only a 6-membered ring in which 2 to 6 benzene rings and / or pyridine rings are linked and / or condensed is not particularly limited. For example, the following (A1) to (A186) (* Represents a connecting part).

Among these, only 6-membered rings in which 2 to 6 benzene rings and / or pyridine rings are connected and / or condensed (the number of condensed rings is 4 or less) in terms of good performance as an organic electroluminescent device material. It is preferable that 2 to 6 benzene rings and / or pyridine rings are connected and / or condensed (the number of condensed rings is 4 or less, and the number of connections is limited to 4) 6 More preferably, it is an aromatic group consisting only of member rings.

The preferred substituents are (A1) to (A19), (A21), (A28), (A30), (A32), (A36), (A38), (A40), (A42) to (A60). , (A63), (A64), (A66) to (A74), (A76), (A78), (A80), (A82), (A84), (A86) to (A124), (A129), ( A130), (A145) to (A154), and (A156) to (A179) are more preferable.

Among these substituents, (A1) to (A19), (A28), (A30), (A32), (A36), (A38), (A40), (A42) to (A44), ( (A47), (A49), (A51), (A54) to (A60), (A63), (A66), (A67), (A72), (A73), (A86) to (A100), (A103) To (A118), (A145) to (A150), (A156) to (A176) are more preferred.

The pyrimidyl group having at least one substituent selected from the group consisting of a methyl group, an alkyl group having 2 to 10 carbon atoms, and an aromatic hydrocarbon group having 6 to 18 carbon atoms is not particularly limited, For example, 4-methylpyrimidin-2-yl group, 5-methylpyrimidin-2-yl group, 2-methylpyrimidin-4-yl group, 6-methylpyrimidin-4-yl group, 2-methylpyrimidin-5-yl Group, 4,6-dimethylpyrimidin-2-yl group, 4-ethylpyrimidin-2-yl group, 5-ethylpyrimidin-2-yl group, 2-ethylpyrimidin-4-yl group, 6-ethylpyrimidine-4 -Yl group, 2-ethylpyrimidin-5-yl group, 4,6-diethylpyrimidin-2-yl group, 4-propylpyrimidin-2-yl group, 5-butylpyrimidin-2 Yl group, 2-pentylpyrimidin-4-yl group, 6-hexylpyrimidin-4-yl group, 2-octylpyrimidin-5-yl group, 4-phenylpyrimidin-2-yl group, 5-phenylpyrimidin-2- Yl group, 2-phenylpyrimidin-4-yl group, 6-phenylpyrimidin-4-yl group, 2-phenylpyrimidin-5-yl group, 4,6-diphenylpyrimidin-2-yl group, 4-naphthylpyrimidine- 2-yl group, 5-naphthylpyrimidin-2-yl group, 2-naphthylpyrimidin-4-yl group, 6-naphthylpyrimidin-4-yl group, 2-naphthylpyrimidin-5-yl group, 6-naphthyl-4 -Phenylpyrimidin-2-yl group, 4,6-dinaphthylpyrimidin-2-yl group, 4-anthracylpyrimidin-2-yl group, 5-anthraci Pyrimidin-2-yl group, 2-anthracylpyrimidin-4-yl group, 6-anthracylpyrimidin-4-yl group, 2-anthracylpyrimidin-5-yl group, 4-phenanthrylpyrimidin-2-yl Group, 5-phenanthrylpyrimidin-2-yl group, 2-phenanthrylpyrimidin-4-yl group, 6-phenanthrylpyrimidin-4-yl group, 2-phenanthrylpyrimidin-5-yl group, 4-pyrenylpyrimidin-2-yl group, 5-pyrenylpyrimidin-2-yl group, 2-pyrenylpyrimidin-4-yl group, 6-pyrenylpyrimidin-4-yl group, 2-pyrenylpyrimidin- Examples include 5-yl group and 4-methyl-6-phenylpyrimidin-2-yl group.

Of these, a pyrimidyl group having at least one substituent selected from the group consisting of a methyl group and an aromatic hydrocarbon group having 6 to 18 carbon atoms is preferable from the viewpoint of good performance as an organic electroluminescent element material. And a pyrimidyl group having at least one substituent selected from the group consisting of a methyl group, a biphenyl group, a phenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group.

The preferred substituents include 5-methylpyrimidin-2-yl group, 4,6-dimethylpyrimidin-2-yl group, 4-phenylpyrimidin-2-yl group, 5-phenylpyrimidin-2-yl group, 2 -Phenylpyrimidin-5-yl group, 4,6-diphenylpyrimidin-2-yl group, 5-naphthylpyrimidin-2-yl group, 6-naphthyl-4-phenylpyrimidin-2-yl group, 5-anthracylpyrimidine A -2-yl group, a 5-phenanthrylpyrimidin-2-yl group, and a 5-pyrenylpyrimidin-2-yl group are more preferable.

Among these substituents, a 5-methylpyrimidin-2-yl group, a 4,6-dimethylpyrimidin-2-yl group, a 4-phenylpyrimidin-2-yl group, and a 5-phenylpyrimidin-2-yl group 2-phenylpyrimidin-5-yl group, 4,6-diphenylpyrimidin-2-yl group, and 5-naphthylpyrimidin-2-yl group are more preferable.

The alkyl group having 2 to 10 carbon atoms, alkoxy group, alkoxyalkyl group, ester group, or ester alkyl group is not particularly limited, and examples thereof include an ethyl group (-Et), an n-propyl group (n- Pr), i-propyl group (i-Pr), n-butyl group (n-Bu), t-butyl group (t-Bu), pentyl (-Pent), hexyl group (-Hex), heptyl group (- Hept), octyl group (—Oct) (above, alkyl group having 2 to 10 carbon atoms), ethoxy group, n-propyloxy group, i-propyloxy group, n-butyloxy group, t-butyloxy group, pentyloxy group Hexyloxy group, heptyloxy group, octyloxy group (above, alkoxy group having 2 to 10 carbon atoms), methoxymethyl group, methoxyethyl group, methoxypropiyl Group, methoxybutyl group, methoxyhexyl group, methoxyheptyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group, pentyloxypropyl group (above, alkyl alkoxy group having 2 to 10 carbon atoms), methyl ester Group, ethyl ester group, n-propyl ester group, i-propyl ester group, n-butyl ester group, t-butyl ester group, pentyl ester group, hexyl ester group, heptyl ester group (above, having 2 to 10 carbon atoms) Ester group), -CH ₂ COOMe, -CH ₂ COOEt, -CH ₂ COO (n-Pr), -CH ₂ COO (i-Pr), -CH ₂ COO (n-Bu), -CH ₂ COO (t -Bu), -CH ₂ COOHex, -CH ₂ CH ₂ CH ₂ COOMe, -CH ₂ CH ₂ CH ₂ COOEt, —CH ₂ CH ₂ CH ₂ COO (n-Pr), —CH ₂ CH ₂ CH ₂ COO (i-Pr), —CH ₂ CH ₂ CH ₂ COO (n-Bu), —CH ₂ CH ₂ CH ₂ COO (t-Bu), —Hex-COOMe (above, ester alkyl group having 2 to 10 carbon atoms) and the like.

The substituents represented by Ar ¹ and Ar ² are not particularly limited, but the following substituents represented by (B1) to (B137) are exemplified in addition to the substituents shown above. (* Represents a connecting part).

As for Ar ¹ and Ar ² , a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a compound having an excellent performance as an organic electroluminescent element material, or Aromatic groups consisting only of 6-membered rings in which 2 to 6 benzene rings and / or pyridine rings are linked and / or condensed {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, carbon A substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group. It may be substituted with at least one)}.

Among the above substituents, a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 5 linked benzene rings and / or pyridine rings and / or Or an aromatic group composed only of a condensed 6-membered ring {these groups include a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, or a pyrimidyl group ( The pyrimidyl group may be substituted with at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group. It is more preferable.

Among these, a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 4 linked and / or condensed rings of a benzene ring and / or a pyridine ring An aromatic group consisting of only a 6-membered ring {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, or a pyrimidyl group (the pyrimidyl group) May be substituted with at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group)} It is more preferable that

Ar ¹ and Ar ² are phenyl, naphthyl, anthracyl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl, and isoquinolyl groups in terms of performance as a compound organic electroluminescent device material. Naphthylidyl group, benzoquinolyl group, phenanthridyl group, acridyl group, phenanthroyl group, biphenyl group, terphenyl group, naphthylphenyl group, phenanthrylphenyl group, anthracylphenyl group, pyrenylphenyl group, naphthylbiphenyl group, Nantrilbiphenyl, Anthracylbiphenyl, Phenylnaphthyl, Binaphthyl, Phenanthrylnaphthyl, Anthracylnaphthyl, Phenylanthracyl, Phenylphenanthryl, Pyridylphenyl, Pyridylbipheny Group, pyridylnaphthyl group, pyridylanthracyl group, pyridylphenanthryl group, quinolylphenyl group, quinolylbiphenyl group, quinolylnaphthyl group, quinolylanthracyl group, quinolylphenanthryl group, isoquinolylphenyl group, isoquinolyl group Quinolylbiphenyl group, isoquinolylnaphthyl group, isoquinolylanthracyl group, isoquinolylphenanthryl group, naphthyridylphenyl group, naphthyridylbiphenyl group, benzoquinolylphenyl group, phenanthridylphenyl group, acridyl Phenyl group, phenanthrylyl group, phenylpyridyl group, diphenylpyridyl group, biphenylpyridyl group, naphthylpyridyl group, phenanthrylpyridyl group, anthracylpyridyl group, phenylquinolyl group, biphenylquinolyl group, phenylisoquinol group Nori Group, biphenylisoquinolyl group, bipyridyl group, quinolylpyridyl group, isoquinolylpyridyl group, pyridylquinolyl group, pyridylisoquinolyl group, phenylbipyridyl group, bipyridylphenyl group, phenylpyridylphenyl group, phenylpyridylnaphthyl group, diphenylpyridyl group Phenyl group, dinaphthylpyridylphenyl group, phenylpyrimidyl group, diphenylpyrimidyl group, biphenylpyrimidyl group, naphthylpyrimidyl group, phenanthrylpyrimidyl group, or anthracylpyrimidyl group {these Is selected from the group consisting of a methyl group, a methoxy group, a fluorine atom, and a pyrimidyl group (the pyrimidyl group is a methyl group, an alkyl group having 2 to 10 carbon atoms, and an aromatic hydrocarbon group having 6 to 18 carbon atoms). May have at least one substituent) Or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, it is preferable that a may be substituted by an ester group or ester alkyl}.

The preferred substituents are phenyl, naphthyl, anthracyl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, naphthyridyl, benzoquinolyl, phenanthridyl, acridyl, phenanthryl Group, biphenyl group, terphenyl group, naphthylphenyl group, phenanthrylphenyl group, anthracylphenyl group, pyrenylphenyl group, naphthylbiphenyl group, phenanthrylbiphenyl group, anthracylbiphenyl group, phenylnaphthyl group, binaphthyl group Phenanthryl naphthyl group, anthracyl naphthyl group, phenyl anthracyl group, phenyl phenanthryl group, pyridyl phenyl group, pyridyl biphenyl group, pyridyl naphthyl group, pyridyl anthracyl group, pyr Ruphenanthryl group, quinolylphenyl group, quinolylbiphenyl group, quinolylnaphthyl group, quinolylanthracyl group, quinolylphenanthryl group, isoquinolylphenyl group, isoquinolylbiphenyl group, isoquinolylnaphthyl group, iso Quinolyl anthracyl group, isoquinolyl phenanthryl group, naphthyridyl phenyl group, naphthyridyl biphenyl group, benzoquinolyl phenyl group, phenanthridyl phenyl group, acridyl phenyl group, phenanthryl phenyl group, phenyl pyridyl Group, diphenylpyridyl group, biphenylpyridyl group, naphthylpyridyl group, phenanthrylpyridyl group, anthracylpyridyl group, phenylquinolyl group, biphenylquinolyl group, phenylisoquinolyl group, biphenylisoquinolyl group, bipyridyl group, Kinori Pyridyl group, isoquinolylpyridyl group, pyridylquinolyl group, pyridylisoquinolyl group, phenylbipyridyl group, bipyridylphenyl group, phenylpyridylphenyl group, phenylpyridylnaphthyl group, diphenylpyridylphenyl group, dinaphthylpyridylphenyl group, phenylpyrimimi Zyl group, diphenylpyrimidyl group, biphenylpyrimidyl group, naphthylpyrimidyl group, phenanthrylpyrimidyl group, or anthracylpyrimidyl group {these groups are methyl group, methoxy group, fluorine atom , A pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group), or a carbon number 2-10 alkyl groups, alkoxy Group, an alkoxyalkyl group, an ester group or an ester alkyl may be substituted} is more preferable.

In addition, phenyl group, naphthyl group, anthracyl group, phenanthryl group, pyrenyl group, pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, naphthyridyl group, benzoquinolyl group, phenanthridyl group, acridyl group, phenanthrolyl group, biphenyl group, tel Phenyl, naphthylphenyl, phenanthrylphenyl, anthracylphenyl, phenylnaphthyl, phenylanthracyl, pyridylphenyl, pyridylbiphenyl, pyridylnaphthyl, quinolylphenyl, quinolylbiphenyl, iso Quinolylphenyl group, isoquinolylbiphenyl group, naphthyridylphenyl group, naphthyridylbiphenyl group, benzoquinolylphenyl group, phenanthridylphenyl group, acridylphenyl group, phenanthroylphenol Group, phenylpyridyl group, diphenylpyridyl group, biphenylpyridyl group, naphthylpyridyl group, phenylquinolyl group, phenylisoquinolyl group, bipyridyl group, phenylbipyridyl group, bipyridylphenyl group, phenylpyridylphenyl group, diphenylpyridylphenyl group , Phenylpyrimidyl group, diphenylpyrimidyl group, biphenylpyrimidyl group or naphthylpyrimidyl group {these groups are methyl group, methoxy group, fluorine atom, pyrimidyl group (the pyrimidyl group is methyl group, (It may have at least one substituent selected from the group consisting of a phenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group), or an alkyl group, alkoxy group, alkoxyalkyl having 2 to 10 carbon atoms Group, ester group or And more preferably substituted also be} in stell alkyl.

In addition, an aromatic group consisting of only a 6-membered ring in which 2 to 5 benzene rings and / or pyridine rings are linked and / or condensed, and 2 to 4 benzene rings and / or pyridine rings linked and / or condensed rings The aromatic group consisting of only the 6-membered ring is not particularly limited, but is an aromatic group consisting of only the 6-membered ring in which 2 to 6 benzene rings and / or pyridine rings are connected and / or condensed. Substituents similar to the substituents exemplified for the group can be exemplified.

Preferred substituents for Ar ¹ and Ar ² are phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 5-phenylpyrimidine- 2-yl group, 4,6-diphenylpyrimidin-2-yl group, 5-naphthylpyrimidin-2-yl group, 4,6-dinaphthylpyrimidin-2-yl group, 5-phenanthrylpyrimidin-2-yl Group, 5-anthracylpyrimidin-2-yl group, 5-pyrenylpyrimidin-2-yl group, or (A1) to (A19), (A21), (A28), (A30), (A32), ( (A36), (A38), (A40), (A42) to (A60), (A63), (A64), (A66) to (A74), (A76), (A78), (A80), (A82) (A84), (A86) to (A124), (A129), (A130), (A145) to (A154), (A156) to (A179), (B1), (B8), (B10), (B20) ), (B26) to (B28), (B30), (B33), (B38), (B52), (B63) to (B70), (B79) to (B82), (B84), (B85), Substituents represented by (B89), (B93), (B98), (B109), (B110), (B117), (B119) to (B126), or (B129) to (B137) are more preferable.

Among these substituents, phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 5-phenylpyrimidin-2-yl Group, 4,6-diphenylpyrimidin-2-yl group, 4,6-dinaphthylpyrimidin-2-yl group, or (A1) to (A19), (A28), (A30), (A32), (A36 ), (A38), (A40), (A42) to (A44), (A47), (A49), (A51), (A54) to (A60), (A63), (A66), (A67), (A72), (A73), (A86) to (A100), (A103) to (A118), (A145) to (A150), (A156) to (A176), (B1), (B26), (B27) ), (B33), ( 38), (B52), (B63) to (B67), (B79) to (B81), (B93), (B98), (B117), (B119) to (B126), or (B129) to (B136) ) Is more preferable.

In the general formula (1), A represents the above general formula (2-1), general formula (2-2), or general formula (2-3).

General formula (2-1), general formula (2-2), and general formula (2-3) will be described.

In general formula (2-1), general formula (2-2), and general formula (2-3), * represents a linking moiety.

Ar ³ , Ar ⁴ and Ar ⁵ are each an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom, alkyl group having 2 to 10 carbon atoms, alkoxy group, And may be substituted with an alkoxyalkyl group, an ester group or an ester alkyl group).

The aromatic hydrocarbon group having 6 to 12 carbon atoms is not particularly limited, and examples thereof include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, and a 4- Biphenyl group etc. are mentioned.

The pyridyl group and pyrimidyl group, not particularly limited, can be exemplified the same substituents as the substituents exemplified for Ar ¹ and Ar ^2.

The alkyl group having 2 to 10 carbon atoms, alkoxy group, alkoxyalkyl group, ester group, or ester alkyl group is not particularly limited, but the same substituents as those exemplified for Ar ¹ and Ar ² are exemplified. can do.

The substituents represented by Ar ³ , Ar ⁴ and Ar ⁵ are not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, 2, 3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2-ethylphenyl Group, 3-ethylphenyl group, 4-ethylphenyl group, 2-ethyl-3-methylphenyl group, 2-ethyl-4-methylphenyl group, 2-ethyl-5-methylphenyl group, 2-ethyl-6- Methylphenyl group, 3-ethyl-2-methylphenyl group, 3-ethyl-4-methylphenyl group, 3-ethyl-5-methylphenyl group, 3-ethyl-6-methylphenyl Nyl group, 4-ethyl-2-methylphenyl group, 4-ethyl-3-methylphenyl group, 2-hexylphenyl group, 3-hexylphenyl group, 4-hexylphenyl group, 4-hexyl-2-methylphenyl group 4-hexyl-3-ethylphenyl group, 4-hexyloxy-2-propylphenyl group, 4-hexyloxy-3-butylphenyl group, 3-ethoxyethyl-5-methylphenyl group, 3-ethoxyethyl-6 -Methylphenyl group, 2-methyl ester phenyl group, 3-methyl ester phenyl group, 4-methyl ester phenyl group, 2-hexyl ester phenyl group, 3-hexyl ester phenyl group, 4-hexyl ester phenyl group, 2- (2-pyridyl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) pheny Group, 3,5-bi (2-pyridyl) phenyl group, 2- (3-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 3,5-bi (3-pyridyl) phenyl group, 2- (4-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 3,5-bi (4-pyridyl) phenyl group 2- (2-pyrimidyl) phenyl group, 3- (2-pyrimidyl) phenyl group, 4- (2-pyrimidyl) phenyl group, 2- (4-pyrimidyl) phenyl group, 3- (4-pyrimidyl) phenyl group 4- (4-pyrimidyl) phenyl group, 2- (5-pyrimidyl) phenyl group, 3- (5-pyrimidyl) phenyl group, 4- (5-pyrimidyl) phenyl group, 2-fluorophenyl group, 3-fluoro Phenyl group, -Fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, perfluorophenyl group, 1-naphthyl group, 2-naphthyl group Group, 2-methylnaphthalen-1-yl group, 3-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group, 5-methylnaphthalen-1-yl group, 6-methylnaphthalen-1-yl Group, 1-methylnaphthalen-2-yl group, 3-methylnaphthalen-2-yl group, 4-methylnaphthalen-2-yl group, 5-methylnaphthalen-2-yl group, 6-methylnaphthalen-2-yl 2-hexylnaphthalen-1-yl group, 3-hexyloxynaphthalen-1-yl group, 4-methoxyethylnaphthalen-1-yl group, 5-hexyl Silester naphthalen-1-yl group, 6-pentoxynaphthalen-1-yl group, 1-methoxyethylnaphthalen-2-yl group, 3-pentylnaphthalen-2-yl group, 4-pentoxynaphthalen-2-yl group Group, 5-methoxyethylnaphthalen-2-yl group, 6-butylnaphthalen-2-yl group, 3- (2-pyridyl) naphthalen-1-yl group, 4- (2-pyridyl) naphthalen-1-yl group 3- (3-pyridyl) naphthalen-1-yl group, 4- (3-pyridyl) naphthalen-1-yl group, 3- (4-pyridyl) naphthalen-1-yl group, 4- (4-pyridyl) Naphthalen-1-yl group, 4- (2-pyridyl) naphthalen-2-yl group, 6- (2-pyridyl) naphthalen-2-yl group, 7- (2-pyridyl) naphthalen-2-yl group, 4 - 3-pyridyl) naphthalen-2-yl group, 6- (3-pyridyl) naphthalen-2-yl group, 7- (3-pyridyl) naphthalen-2-yl group, 4- (4-pyridyl) naphthalene-2- Yl group, 6- (4-pyridyl) naphthalen-2-yl group, 7- (4-pyridyl) naphthalen-2-yl group, 3- (2-pyrimidyl) naphthalen-1-yl group, 4- (2- Pyrimidyl) naphthalen-1-yl group, 3- (4-pyrimidyl) naphthalen-1-yl group, 4- (4-pyrimidyl) naphthalen-1-yl group, 3- (5-pyrimidyl) naphthalen-1-yl group 4- (5-pyrimidyl) naphthalen-1-yl group, 4- (2-pyrimidyl) naphthalen-2-yl group, 6- (2-pyrimidyl) naphthalen-2-yl group, 7- (2-pyrimidyl) Naphthalene-2- 4- (4-pyrimidyl) naphthalen-2-yl group, 6- (4-pyrimidyl) naphthalen-2-yl group, 7- (4-pyrimidyl) naphthalen-2-yl group, 4- (5- Pyrimidyl) naphthalen-2-yl group, 6- (5-pyrimidyl) naphthalen-2-yl group, 7- (5-pyrimidyl) naphthalen-2-yl group, 2-fluoronaphthalen-1-yl group, 3-fluoro Naphthalen-1-yl group, 4-fluoronaphthalen-1-yl group, 5-fluoronaphthalen-1-yl group, 6-fluoronaphthalen-1-yl group, 1-fluoronaphthalen-2-yl group, 3-fluoro Naphthalen-2-yl group, 4-fluoronaphthalen-2-yl group, 5-fluoronaphthalen-2-yl group, 6-fluoronaphthalen-2-yl group, perfluoronaphthalene- 1-yl group, perfluoronaphthalen-2-yl group, 3-biphenyl group, 4-biphenyl group, 2-methylbiphenyl-3-yl group, 4-methylbiphenyl-3-yl group, 5-methylbiphenyl-3 -Yl group, 6-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 3'-methylbiphenyl-3-yl group, 4'-methylbiphenyl-3-yl group, 2,6 -Dimethylbiphenyl-3-yl group, 2 ', 6'-dimethylbiphenyl-3-yl group, 2-methylbiphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4 -Yl group, 3'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,6-dimethylbiphenyl-4-yl group, 2 ', 6'-dimethylbiphenyl-4-yl Group, 2-hex Silbiphenyl-3-yl group, 4-hexyloxybiphenyl-3-yl group, 5-ethylethoxyethylbiphenyl-3-yl group, 6-hexyl ester biphenyl-3-yl group, 2'-pentylbiphenyl-3- Yl group, 3′-pentyloxybiphenyl-3-yl group, 4′-propyloxymethyl-3-yl group, 2-butylbiphenyl-4-yl group, 3-butoxybiphenyl-4-yl group, 2′- Ethoxymethylbiphenyl-4-yl group, 3′-butyl ester biphenyl-4-yl group, 4′-pentylbiphenyl-4-yl group, 3 ′-(2-pyridyl) biphenyl-3-yl group, 3′- (3-pyridyl) biphenyl-3-yl group, 3 ′-(4-pyridyl) biphenyl-3-yl group, 4 ′-(2-pyridyl) biphenyl-3-yl group, 4 ′-(3-pyridyl group) B) Biphenyl-3-yl group, 4 ′-(4-pyridyl) biphenyl-3-yl group, 3 ′-(2-pyridyl) biphenyl-4-yl group, 3 ′-(3-pyridyl) biphenyl-4 -Yl group, 3 '-(4-pyridyl) biphenyl-4-yl group, 4'-(2-pyridyl) biphenyl-4-yl group, 4 '-(3-pyridyl) biphenyl-4-yl group, 4 '-(4-pyridyl) biphenyl-4-yl group, 3'-(2-pyrimidyl) biphenyl-3-yl group, 3 '-(4-pyrimidyl) biphenyl-3-yl group, 3'-(5- Pyrimidyl) biphenyl-3-yl group, 4 ′-(2-pyrimidyl) biphenyl-3-yl group, 4 ′-(4-pyrimidyl) biphenyl-3-yl group, 4 ′-(5-pyrimidyl) biphenyl-3 -Yl group, 3 '-(2-pyrimidyl) biphenyl-4-yl group 3 ′-(4-pyrimidyl) biphenyl-4-yl group, 3 ′-(5-pyrimidyl) biphenyl-4-yl group, 4 ′-(2-pyrimidyl) biphenyl-4-yl group, 4 ′-(4 -Pyrimidyl) biphenyl-4-yl group, 4 '-(5-pyrimidyl) biphenyl-4-yl group, 2-fluorobiphenyl-3-yl group, 4-fluorobiphenyl-3-yl group, 5-fluorobiphenyl- 3-yl group, 6-fluorobiphenyl-3-yl group, 2′-fluorobiphenyl-3-yl group, 3′-fluorobiphenyl-3-yl group, 4′-fluorobiphenyl-3-yl group, 2, 6-difluorobiphenyl-3-yl group, 2 ′, 6′-difluorobiphenyl-3-yl group, 2-fluorobiphenyl-4-yl group, 3-fluorobiphenyl-4-yl group, 2′-fluorobiphenyl Ru-4-yl group, 3′-fluorobiphenyl-4-yl group, 4′-fluorobiphenyl-4-yl group, 2,6-difluorobiphenyl-4-yl group, 2 ′, 6′-difluorobiphenyl- 4-yl group and the like can be mentioned.

Ar ³ , Ar ^4, and Ar ⁵ are aromatic hydrocarbon groups having 6 to 12 carbon atoms (methyl group, methoxy group, alkyl group having 2 to 10 carbon atoms or An alkoxy group, a pyridyl group, a pyrimidyl group, or a fluorine atom, which may be substituted).

The preferred substituent is more preferably a phenyl group, a naphthyl group, or a biphenyl group (these groups may be substituted with a methyl group, a methoxy group, a pyridyl group, a pyrimidyl group, or a fluorine atom). preferable.

Further, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 1-naphthyl group, 2-naphthyl group, 3-biphenyl group, 4-biphenyl group, 2,6-dimethylbiphenyl- 3-yl group, 2,6-dimethylbiphenyl-4-yl group, 2 ′, 6′-dimethylbiphenyl-3-yl group, 2 ′, 6′-dimethylbiphenyl-4-yl group, 3- (2- Pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 4- (4- More preferred is a pyridyl) phenyl group, a 3- (2-pyrimidyl) phenyl group, or a 4- (2-pyrimidyl) phenyl group.

Among these substituents, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-biphenyl group, 4-biphenyl group, 1-naphthyl group, or 2-naphthyl group It is more preferable that

Ar ³ , Ar ^4, and Ar ⁵ are phenyl, naphthyl, or biphenyl groups (these groups are methyl, methoxy, pyridyl, pyrimidyl, etc.) because they have good performance as organic electroluminescent device materials. Group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, which may be substituted).

Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a methyl group, a methoxy group, a fluorine atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom) Or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group.

Aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom, or alkyl group, alkoxy group, alkoxyalkyl group, ester group or ester alkyl group having 2 to 10 carbon atoms) Can be substituted with the same substituents as exemplified for Ar ³ , Ar ⁴ and Ar ⁵ .

Ar ⁶ and Ar ⁷ are a hydrogen atom, a methyl group, a methoxy group, a fluorine atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group) in terms of good performance as an organic electroluminescent element material. And an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a pyridyl group, a pyrimidyl group, or a fluorine atom, which may be substituted.

For the preferred substituent, a phenyl group, a naphthyl group, or a biphenyl group (these groups may be substituted with a methyl group, a methoxy group, a pyridyl group, a pyrimidyl group, or a fluorine atom), a hydrogen atom, a methyl group It is more preferably a group, a methoxy group, or a fluorine atom.

Further, hydrogen atom, methyl group, methoxy group, fluorine atom, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 1-naphthyl group, 2-naphthyl group, 3-biphenyl group, 4-biphenyl group, 2,6-dimethylbiphenyl-3-yl group, 2,6-dimethylbiphenyl-4-yl group, 2 ′, 6′-dimethylbiphenyl-3-yl group, 2 ′, 6′-dimethyl Biphenyl-4-yl group, 3- (2-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 4- ( A 3-pyridyl) phenyl group, a 4- (4-pyridyl) phenyl group, a 3- (2-pyrimidyl) phenyl group, or a 4- (2-pyrimidyl) phenyl group is more preferable.

Among these substituents, a hydrogen atom, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-biphenyl group, 4-biphenyl group, 1-naphthyl group, or 2 -It is more preferably a naphthyl group.

Further, among these substituents, a hydrogen atom, a phenyl group, a 3-biphenyl group, and a 4-biphenyl group are more preferable.

Ar ⁶ and Ar ⁷ are phenyl group, naphthyl group, or biphenyl group (these groups are methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine, etc.) in terms of good performance as an organic electroluminescent element material. An atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group), a hydrogen atom, a methyl group, a methoxy group, or a fluorine atom. preferable.

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ and R ³² are each independently a hydrogen atom, It represents a methyl group, a methoxy group, a phenyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group.

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ and R ³² and 2 to 10 carbon atoms The alkyl group, the alkoxy group, the alkoxyalkyl group, the ester group, or the ester alkyl group is not particularly limited, and examples thereof are the same as those exemplified for Ar ¹ and Ar ² .

For R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ and R ³² , the organic electroluminescent element of the compound In terms of good performance as a material, each is preferably independently a hydrogen atom, a methyl group, a methoxy group, a phenyl group, or a fluorine atom, and more preferably a hydrogen atom, a methyl group, a methoxy group, or a phenyl group. Preferably, it is a hydrogen atom.

Note that each hydrogen atom in the compound (1) may be independently a deuterium atom.

Compound (1) is not particularly limited, but can be exemplified by the following (C1) to (C1076).

Next, the manufacturing method of the present invention will be described.

The compound (1) of the present invention has the following reaction formula

(In the formulas (1), (3), (4) and (5), Z ¹ and Z ² each independently represent a leaving group, and M ¹ and M ² each independently represent a metal group, boron Represents an acid group or a boronic acid ester group, and other symbols are as defined above.)
It can be manufactured by the method shown in

Hereinafter, the compound represented by the general formula (3) is referred to as a compound (3). The same applies to compound (4) and compound (5). Compound (4) and compound (5) can be produced, for example, using the method disclosed in JP 2008-280330 A [0061] to [0076].

Examples of the compound (3) include the following (D1) to (D81), but the present invention is not limited to these. Here, Z ¹ and Z ² each independently represent a leaving group described later.

The compound (4) and the compound (5), the above (A1) ~ (A186) and (B1) ~ (B137) Compound of * was changed to ^{M 1} in, and the following (E1) ~ (E19) However, the present invention is not limited to these examples. Here, M ¹ represents a metal group, a boronic acid group, or a boronic acid ester group.

Hereinafter, although a specific example is given and demonstrated about "process 1", this invention is not limited to these.

“Step 1” is a step of synthesizing compound (1).

Compound (1) is synthesized by reacting compound (3) with compound (4) in the presence of a metal catalyst or in the presence of a metal catalyst and a base, and then reacting compound (5). By applying reaction conditions for general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the desired product can be obtained in high yield.

In the “Step 1”, the reaction order of the compound (4) and the compound (5) may be reversed. In addition, the compound (4) and the compound (5) may be reacted sequentially in one pot, or the intermediate product may be taken out once in the stage where the compound (4) is reacted, and the compound (5) may be reacted separately. .

Examples of M ¹ and M ² in the compound (4) and the compound (5) are not particularly limited. For example, ZnX ¹ , MgX ² , Sn (X ³ ) ₃ , B (OX ⁴ ) ₂ Etc. However, X ¹ and X ² each independently represent a chlorine atom, a bromine atom or an iodine atom, X ³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and X ⁴ represents a hydrogen atom and 1 carbon atom. represents an alkyl group or a phenyl group having 4, B ^(OX ₄₎ 2 two ^{X 4} ₂ may be the same or different. Also, two X ⁴ can also form a ring containing an oxygen atom and a boron atom together.

B (OX ⁴ ) ₂ in the compound (4) and the compound (5) is not particularly limited. For example, B (OH) ₂ , B (OMe) ₂ , B (O ⁱ Pr) ₂ , B (OBu) ₂ , B (OPh) _{2 and the} like can be exemplified. Examples of B (OX ⁴ ) ₂ in the case where two X ⁴ are united to form a ring containing an oxygen atom and a boron atom include groups represented by the following (F1) to (F6): The group represented by (F2) is preferable because it can be exemplified and the yield is good.

The leaving group represented by Z ¹ and Z ² in the compound (3) is not particularly limited, and examples thereof include a chlorine group, a bromine group, an iodine group, a trifluoromethylsulfonyloxy (OTf) group, and methane. Examples thereof include a sulfonyloxy group, a chloromethanesulfonyloxy group, and a p-toluenesulfonyloxy group.

Examples of the metal catalyst that can be used in “Step 1” include a palladium catalyst and a nickel catalyst.

The palladium catalyst that can be used in “Step 1” is not particularly limited, and examples thereof include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, and the like. In addition, π-allyl palladium chloride dimer, palladium acetylacetonate, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro [1,1′-bis (diphenylphosphine). Fino) ferrocene] complex compounds such as palladium. Among these, a palladium complex having a tertiary phosphine as a ligand is preferable in terms of a good reaction yield.

A palladium complex having tertiary phosphine as a ligand can also be prepared in a reaction system by adding tertiary phosphine to a palladium salt or complex compound. The tertiary phosphine that can be used in this case is not particularly limited. For example, 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-butylphosphino ) 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 (diphenylphosphine) Fino) -1,1′-binaphthyl, 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl and the like. 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl is preferred because it is readily available and the reaction yield is good.

The molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield.

Further, the nickel catalyst that can be used in “Step 1” is not particularly limited. For example, [1,1′-bis (diphenylphosphino) ferrocene] nickel (II) dichloride, [1,2 -Bis (diphenylphosphino) ethane] nickel (II) dichloride, [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride, [1,1'-bis (diphenylphosphino) propane] nickel ( II) Dichloride, 1,2-bis (diphenylphosphino) ethane] nickel (II) dichloride, [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride, and the like.

The base that can be used in “Step 1” is not particularly limited, and examples thereof include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, tripotassium phosphate, and phosphoric acid. Sodium, sodium fluoride, potassium fluoride, cesium fluoride and the like can be exemplified, and tripotassium phosphate is desirable in terms of a good yield. The molar ratio of the base to the compound (3), the compound (4) and the compound (5) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of a good yield.

In “Step 1”, a solvent can be used, and it is preferable to use a solvent from the viewpoint of controlling the reaction. The solvent that can be used in “Step 1” is not particularly limited, and examples thereof include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, dioxane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene. These may be used in appropriate combination. It is desirable to use a mixed solvent of dioxane and water and a mixed solvent of tetrahydrofuran and water in terms of a good yield.

“Step 1” can be performed at a temperature appropriately selected from 0 ° C. to 150 ° C., and is more preferably performed at 80 ° C. to 100 ° C. in terms of a good yield.

Compound (1) can be obtained by performing a normal treatment (separation operation or the like) performed by those skilled in the art after completion of “Step 1”. Furthermore, you may refine | purify by recrystallization, column chromatography, sublimation, etc. as needed.

The compound (3) of the present invention can also be represented as general formula (3-1), general formula (3-2) and general formula (3-3). The compound represented by the general formula (3-1) is referred to as a compound (3-1). The same applies to compound (3-2) and compound (3-3).

Compound (3-1), Compound (3-2) and Compound (3-3) can be produced by the method shown by the following reaction formula.

(Wherein W ¹¹ , W ¹² , W ¹³ , W ²¹ , W ²² , W ²³ , W ³¹ , W ³² and W ³³ represent substituents necessary for carrying out the pyrimidine ring formation reaction, and Z ¹¹ , Z ¹² , Z ²¹ , Z ²² , Z ³¹ and Z ³² each independently represent a leaving group, and the substituents represented by the other symbols are the same as those described above.
Hereinafter, the compound represented by the general formula (6-1) is referred to as a compound (6-1). The same applies to compound (6-2), compound (6-3), compound (7-1), compound (7-2), and compound (7-3).

Hereinafter, although a specific example is given and demonstrated about "the process 2," this invention is not limited to these.

“Step 2” is a step of obtaining compound (3-1), compound (3-2) or compound (3-3).

Compound (3-1) is present in the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base, in the presence or absence of a nitrogen source. Is synthesized by reacting compound (6-1) with compound (7-1).

Compound (3-2) is present in the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base, in the presence or absence of a nitrogen source. Is synthesized by reacting compound (6-2) with compound (7-2).

Compound (3-3) is present in the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base, in the presence or absence of a nitrogen source. Is synthesized by reacting compound (6-3) with compound (7-3).

W ¹¹ , W ¹² , W ^{13 in} Compound (6-1), Compound (6-2), Compound (6-3), Compound (7-1), Compound (7-2) and Compound (7-3) Examples of substituents necessary for carrying out the pyrimidine ring formation reaction represented by W ²¹ , W ²² , W ²³ , W ³¹ , W ³² and W ³³ are not particularly limited. Examples include formyl group, carbonyl group, carboxyl group, ester group, amide group, amino group, imino group, amidyl group or its hydrochloride, nitrile group, and halogen. Of these, an amidyl group or a hydrochloride thereof, a formyl group, a nitrile group, a carbonyl group, an amino group, and an imino group are preferable from the viewpoint of ease of synthesis.

The leaving group represented by Z ¹¹ , Z ¹² , Z ²¹ , Z ²² , Z ³¹ and Z ³² in the compound (3-1), the compound (3-2) or the compound (3-3) is particularly limited. not intended to be, but can be exemplified the same substituents as the substituents exemplified for Z ¹ and Z ^2.

The acid that can be used in “Step 2” is not particularly limited. For example, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, acetic anhydride, formic acid, oxalic acid, ammonium chloride, fluorosulfonic acid, benzene Examples thereof include sulfonic acid and p-toluenesulfonic acid.

The base that can be used in “Step 2” is not particularly limited, and examples thereof include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, tripotassium phosphate, and phosphoric acid. Examples include trisodium, sodium fluoride, potassium fluoride, cesium fluoride, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, and the like.

The catalyst that can be used in “Step 2” is not particularly limited, and examples thereof include halogens, Lewis acids, Lewis bases, or catalytic amounts of the above acids and bases. Examples of the halogen include iodine, bromine, and chlorine. Examples of the Lewis acid and the Lewis base include metal complexes such as indium, ytterbium, zinc, copper, iron, hafnium, and aluminum.

The nitrogen source that can be used in “Step 2” is not particularly limited, and examples thereof include ammonium acetate, ammonium chloride, ammonium formate, ammonium sulfate, ammonium nitrate, ammonium carbonate, ammonium iodide, ammonium fluoride, and hydrogen carbonate. Examples thereof include ammonium, ammonium dihydrogen phosphate, ammonium benzenesulfonate, and ammonium p-toluenesulfonate.

In "Step 2", a solvent can be used, and it is preferable to use a solvent from the viewpoint of reaction control. The solvent that can be used in “Step 2” is not particularly limited, and examples thereof include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, dioxane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene. .

“Step 2” can be performed at a temperature appropriately selected from 0 ° C. to 150 ° C.

The compound (3-1), the compound (3-2) and the compound (3-3) can be obtained by performing a usual treatment (separation operation or the like) performed by those skilled in the art after completion of “Step 2”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.

In addition, the compound (3-1) and the compound (3-2) of the present invention are represented by the following reaction formula:

(Substituents represented by symbols in the formula are the same as those described above.)
It can also be manufactured by the method shown in FIG.

The compound represented by general formula (8-1) is referred to as compound (8-1). The same applies to compound (8-2), compound (9-1) and compound (9-2).

“Step 3” is a step of obtaining the compound (9-1) or the compound (9-2).

Compound (9-1) is prepared in the presence or absence of a nitrogen source in the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base. Is synthesized by reacting compound (6-1) with compound (8-1).

Compound (9-2) is prepared in the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base, in the presence or absence of a nitrogen source. Is synthesized by reacting compound (6-2) with compound (8-2).

The reaction conditions in “Step 3” are the same as those in Step 2.

The compound (9-1) or compound (9-2) obtained in “Step 3” is purified without refining or by recrystallization, column chromatography or sublimation, etc. Can be used as

Hereinafter, “step 4” will be described with specific examples, but the present invention is not limited to these.

“Step 4” is a step of obtaining compound (3-1) or compound (3-2).

The compound (3-1) is synthesized by oxidizing the dihydrobenzoquinazolyl group of the compound (9-1) in the presence of an oxidizing agent and in the presence of an acid or a base.

Compound (3-2) is synthesized by oxidizing the dihydrobenzoquinazolyl group of compound (9-2) in the presence of an oxidizing agent and in the presence of an acid or a base.

Examples of the oxidizing agent that can be used in “Step 4” include potassium permanganate, manganese dioxide, chromium (IV) oxide, sodium dichromate, potassium dichromate, potassium chromate, chromate ester, hydrogen peroxide, 2, Examples include 3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), tetrachloro-1,4-benzoquinone (chloranil), tetrachloro-1,2-benzoquinone (o-chloranil), or nitrobenzene. It is done.

As the acid or base that can be used in “Step 4”, the compounds mentioned in “Step 2” can be used.

In “Step 4”, a solvent can be used, and it is preferable to use a solvent from the viewpoint of controlling the reaction. The solvent that can be used in “Step 4” is not particularly limited, and examples thereof include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, dioxane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene.

“Step 4” can be performed at a temperature appropriately selected from 0 ° C. to 150 ° C.

The compound (3-1) and the compound (3-2) can be obtained by performing a usual treatment (separation operation or the like) performed by those skilled in the art after completion of “Step 4”. Furthermore, you may refine | purify by recrystallization, column chromatography, sublimation, etc. as needed.

The compound (1) of the present application is suitably used as a material for an organic electroluminescence device.

Furthermore, the compound (1) of the present application is suitably used as an electron transport material or an electron injection material for an organic electroluminescence device.

Although there is no limitation in particular in the manufacturing method of the thin film for organic electroluminescent elements containing the compound (1) of this invention, The film-forming by a vacuum evaporation method can be mentioned as a preferable example. Film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus. The vacuum degree of the vacuum chamber when forming a film by the vacuum evaporation method is such that the production tact time for producing the organic electroluminescent element is short and the production cost is superior, so that commonly used diffusion pumps, turbo molecular pumps, cryogenic pumps are used. It is preferably about 1 × 10 ⁻² to 1 × 10 ⁻⁶ Pa that can be reached by a pump or the like, and more preferably 1 × 10 ⁻³ to 10 ⁻⁶ Pa. The deposition rate is preferably 0.005 to 10 nm / second, more preferably 0.01 to 1 nm / second, depending on the thickness of the film to be formed. Moreover, the thin film for organic electroluminescent elements which consists of a compound A can also be manufactured by the solution coating method. For example, compound A is dissolved in an organic solvent such as chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, or tetrahydrofuran, and spin coating, ink jet, casting, or dip using a general-purpose apparatus. It is also possible to form a film by, for example.

The typical structure of the organic electroluminescent element that can obtain the effects of the present invention includes a substrate, an anode, a hole-in layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode.

The anode and cathode of the organic electroluminescent element are connected to a power source through an electrical conductor. The organic electroluminescent device operates by applying a potential between the anode and the cathode. Holes are injected into the organic electroluminescent device from the anode, and electrons are injected into the organic electroluminescent device at the cathode.

The organic electroluminescent element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate. The electrode in contact with the substrate is called the lower electrode for convenience. Generally, the lower electrode is an anode, but the organic electroluminescence device of the present invention is not limited to such a form. The substrate may be light transmissive or opaque, depending on the intended emission direction. Light transmission properties are desirable for viewing electroluminescent emission through a substrate. Transparent glass or plastic is generally employed as such a substrate. The substrate may be a composite structure including multiple material layers.

If an electroluminescent emission is seen through the anode, the anode should pass or substantially pass the emission. Common transparent anode (anode) materials used in the present invention are indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide, but other metal oxides such as Aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide are also useful. 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 where electroluminescent emission is only seen through the cathode, the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium and platinum.

A hole injection layer can be provided between the anode and the hole transport layer. The hole injection material can serve to improve the film forming properties of the subsequent organic layer and to facilitate injection of holes into the hole transport layer. Examples of materials suitable for use in the hole injection layer include porphyrin compounds, plasma deposited fluorocarbon polymers, and amines having aromatic rings such as biphenyl groups and carbazole groups, such as m-MTDATA (4,4 ′ , 4 ″ -tris [(3-methylphenyl) phenylamino] triphenylamine), 2T-NATA (4,4 ′, 4 ″ -tris [(N-naphthalen-2-yl) -N-phenylamino ] Triphenylamine), triphenylamine, tolylamine, 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 and the like can be mentioned.

The hole transport layer of the organic electroluminescence device preferably contains one or more hole transport compounds such as aromatic tertiary amines. Aromatic tertiary amine means that the compound contains one or more trivalent nitrogen atoms, the trivalent nitrogen atoms being bonded only to carbon atoms, one or more of these carbon atoms being An aromatic ring is formed. Specifically, the aromatic tertiary amine can be an arylamine, such as a monoarylamine, diarylamine, triarylamine, or a polymeric arylamine.

As the hole transport material, an aromatic tertiary amine having one or more amine groups can be used. Furthermore, a polymeric hole transport material can be used. For example, poly (N-vinylcarbazole) (PVK), polythiophene, polypyrrole, or polyaniline can 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′-diamine).

Dipyrazino [2,3-f: 2 ′, 3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile as a charge generation layer between the hole injection layer and the hole transport layer A layer containing (HAT-CN) may be provided.

The light emitting layer of the organic electroluminescent element contains a phosphorescent material or a fluorescent material. In this case, light emission occurs as a result of recombination of electron-hole pairs in this region. The emissive layer may consist of a single material including both small molecules and polymers, but more commonly consists of a host material doped with a guest compound, in which case the emission is mainly from the dopant. Occurs and can have any color.

Examples of the host material for the light emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthranyl group. 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 (carbazole-9) -Yl) biphenyl), CDBP (4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl), 9,10-bis (biphenyl) anthracene and the like.

The host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as 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 compounds, thiopyran compounds, polymethine compounds, pyrylium or thiapyrylium compounds, fluorene derivatives, perifanthene derivatives, indeno Examples include perylene derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.

An example of a useful phosphorescent dopant is an organometallic complex of a transition metal of iridium, platinum, palladium, or osmium.

Examples of dopants include Alq ₃ (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) ₃ ( And tris (2-phenylpyridine) iridium (III), 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 transport layer of the organic electroluminescence device of the present invention is the compound (1) of the present application. Note that the electron transporting layer may contain another electron transporting material, and examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Desirable alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include, for example, 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate). Copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, Bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-Crezolate) gallium, bis (2-methyl-8-quinolina) G) -1-naphthoquinone Trad aluminum or bis (2-methyl-8-quinolinato) -2-naphthoquinone Trad gallium, and the like.

A hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance. Desirable compounds for the hole element layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).

In the organic electroluminescent device of the present invention, an electron injection layer may be provided for the purpose of improving the electron injection property and improving device characteristics (for example, light emission efficiency, constant voltage drive, or high durability).

Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, or anthrone. Etc. In addition, the above-described metal complexes, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO _a , AlO _a , SiN _a , SiON, Inorganic compounds such as various oxides, nitrides, and oxynitrides such as AlON, GeO _a , LiO _a , LiON, TiO _a , TiON, TaO _a , TaON, TaN _a , and C ( _a shown here is positive Can also be used).

If light emission is seen only through the anode, the cathode used in the present invention can be formed from almost any conductive material. Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.

Hereinafter, the present invention will be described in more detail with reference to experimental examples and test examples, but the present invention is not limited thereto.

Experimental example-1 (Example)

Α-Tetralone 7.31 g (50.0 mmol) and benzaldehyde 5.31 g (50.0 mmol) were added to 100 mL of acetic acid, and 24.5 g (250 mmol) of concentrated sulfuric acid was added thereto, followed by stirring for 14 hours. Subsequently, 200 mL of water was added to the reaction mixture. The precipitated solid was collected by filtration and washed with water to give the target 2-benzylidene-3,4-dihydro-2H-naphthalen-1-one (A-1) as a light brown powder (yield 10.6 g, yield) 91%).

¹ H-NMR (CDCl ₃ ), δ (ppm): 2.98 (t, J = 6.5 Hz, 2H), 3.16 (t, J = 6.5 Hz, 2H), 7.28 (d, J = 7.5 Hz, 1H), 7.33-7.49 (m, 6H), 7.52 (t, J = 7.5 Hz, 1H), 7.90 (s, 1H), 8.16 ( d, J = 7.8 Hz, 1H).
2-benzylidene-3,4-dihydro-2H-naphthalen-1-one (A-1) 7.26 g (31.0 mmol), 3-bromo-5-chlorobenzamidine hydrochloride 2.70 g (10.0 mmol) Was added to 10 mL of ethanol, and 15 mL of an ethanol solution of potassium hydroxide 1.12 g (20.0 mmol) was added thereto and refluxed for 18 hours. After allowing to cool to room temperature, water is added, and the precipitated solid is collected by filtration to give the desired 2- (3-bromo-5-chlorophenyl) -4-phenyl-5,6-dihydrobenzo [h] quinazoline (A -2) (yield 3.96 g, 88% yield).

¹ H-NMR (CDCl ₃ ), δ (ppm): 2.94 (t, J = 7.2 Hz, 2H), 3.13 (t, J = 7.2 Hz, 2H), 7.30 (d, J = 6.4 Hz, 1H), 7.45-7.60 (m, 5H), 7.63 (s, 1H), 7.73 (d, J = 7.7 Hz, 2H), 8.58 ( d, J = 6.8 Hz, 1H), 8.60 (s, 1H), 8.70 (s, 1H).
2- (3-Bromo-5-chlorophenyl) -4-phenyl-5,6-dihydrobenzo [h] quinazoline (A-2) 3.00 g (6.7 mmol), 2,3-dichloro-5,6- Dicyano-1,4-benzoquinone (DDQ) (3.04 g, 13.4 mmol) was added to o-dichlorobenzene (33 mL), and the mixture was heated and stirred at 120 ° C. for 3 hours. After cooling to room temperature, the precipitated solid was collected by filtration and washed with toluene and methanol. The obtained solid was recrystallized from toluene to obtain the desired 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) white powder (yield 1.22 g, Yield 41%).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.64-7.67 (m, 3H), 7.68 (s, 1H), 7.85-7.88 (m, 3H), 7 91-7.93 (m, 2H), 7.95-7.99 (m, 1H), 8.00 (d, J = 9.1 Hz, 1H), 8.79 (s, 1H), 8 .90 (s, 1H), 9.52-9.55 (m, 1H).
Experimental example-2 (Example)

Under an argon stream, 554 mg (2.91 mmol) of copper iodide and 577 mg (3.20 mmol) of 1,10-phenanthroline were added to 58 mL of DMF, 3.00 g (29.1 mmol) of benzonitrile, 4.25 g of α-tetralone ( 29.1 mmol) and sodium-t-butoxide (16.0 g, 116 mmol) were added, and the mixture was stirred at 80 ° C. for 10 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and washed with water and hexane. The obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform), and the desired 2- (α-aminobenzylidene) -3,4-dihydro-2H-naphthalen-1-one (A′-1) Of light brown powder (yield 4.46 g, 61% yield).

¹ H-NMR (CDCl ₃ ), δ (ppm): 2.50 (t, J = 6.6 Hz, 2H), 2.75 (t, J = 6.6 Hz, 2H), 7.15 (d, J = 7.2 Hz, 1H), 7.35 (td, J = 7.6 Hz, 1.5 Hz, 1H), 7.36 (dd, J = 7.2 Hz, 1.5 Hz, 1H), 7.39. −7.48 (m, 5H), 8.06 (dd, J = 7.5 Hz, 1.7 Hz, 1H).
Under an argon stream, 232 mg (0.924 mmol) of 2- (α-aminobenzylidene) -3,4-dihydro-2H-naphthalen-1-one (A′-1), 300 mg of 3-bromo-5-chlorobenzonitrile ( 1.39 mmol) and 588 mg (2.77 mmol) of tripotassium phosphate were added to 3 mL of DMF, followed by heating and stirring at 80 ° C. for 17 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and washed with water and methanol. The obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain the desired 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) white powder. Body (yield 103 mg, yield 25%).

Experiment-3 (Example)

Under an argon stream, 1.20 g (2.69 mmol) of 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3), 4- (2-pyridyl) phenylboronic acid 18 g (5.92 mmol), palladium acetate 12.1 mg (0.0548 mmol), and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl 76.9 mg (0.161 mmol) were added to THF 19 mL. Further, 4.0 mL of 3M potassium carbonate aqueous solution was added, and the mixture was heated to reflux for 14 hours. After allowing to cool to room temperature, water is added and the precipitated solid is collected by filtration and washed with water, methanol, and hexane to give the desired 4-phenyl-2- [4,4 ″ -bis (2-pyridyl). ) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] benzo [h] quinazoline (A-4) as a light brown powder (yield 1.72 g, yield 100%) .

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.29 (dd, J = 7.1, 4.8 Hz, 2H), 7.63-7.69 (m, 3H), 7.80- 7.89 (m, 7H), 7.95-8.00 (m, 7H), 8.04 (d, J = 9.1 Hz, 1H), 8.10 (s, 1H), 8.21 ( d, J = 8.4 Hz, 4H), 8.77 (d, J = 4.8 Hz, 2H), 9.17 (s, 2H), 9.60-9.62 (m, 1H).
Experimental Example 4 (Example)

Under an argon stream, 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) 1.11 g (2.5 mmol), 1-pyreneboronic acid 738 mg (3.0 mmol), and Bis (triphenylphosphino) palladium (II) dichloride (35.1 mg, 0.050 mmol) was added to THF (25 mL), 3M-potassium carbonate aqueous solution (2.0 mL) was further added, and the mixture was heated to reflux for 13 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The resulting solid was recrystallized with 25 mL of o-xylene to give the desired 2- [3-chloro-5- (1-pyrenyl) phenyl] -4-phenylbenzo [h] quinazoline (B-1) gray powder (Yield 1.12 g, 79% yield).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.61-7.64 (m, 3H), 7.77-7.83 (m, 3H), 7.85 (d, J = 9. 1 Hz, 1H), 7.92-7.94 (m, 2H), 7.96 (d, J = 8.3 Hz, 1H), 8.02 (d, J = 9.1 Hz, 1H), 8. 07 (t, J = 7.6 Hz, 1H), 8.10 (d, J = 9.5 Hz, 1H), 8.14 (d, J = 7.8 Hz, 1H), 8.17 (s, 2H) ), 8.21-8.29 (m, 3H), 8.32 (d, J = 7.8 Hz, 1H), 8.97-9.01 (m, 2H), 9.50 (d, J = 7.6 Hz, 1H).
Under an argon stream, 2- [3-chloro-5- (1-pyrenyl) phenyl] -4-phenylbenzo [h] quinazoline (B-1) 1.10 g (1.94 mmol), 4- (2-pyridyl) 425 mg (2.13 mmol) of phenylboronic acid, 8.7 mg (0.039 mmol) of palladium acetate, and 55.8 mg (0.117 mmol) of 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl were dissolved in THF. In addition to 19 mL, 1.4 mL of 3M potassium carbonate aqueous solution was further added, and the mixture was heated to reflux for 6 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized from toluene to obtain the desired 4-phenyl-2- [5- (1-pyrenyl) -4 ′-(2-pyridyl) biphenyl-3-yl] benzo [h] quinazoline ( A light brown powder (yield 1.19 g, yield 90%) of B-2) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.26-7.29 (m, 1H), 7.54-7.64 (m, 4H), 7.78-7.85 (m, 3H), 7.94-7.96 (m, 3H), 8.03 (d, J = 9.2 Hz, 2H), 8.06-8.23 (m, 9H), 8.26 (d, J = 7.5 Hz, 1H), 8, 31-8.39 (m, 4H), 8.91 (d, J = 4.6 Hz, 1H), 9.15 (s, 1H), 9.29 ( s, 1H), 9.53-9.56 (m, 1H).
Experimental Example-5 (Example)

Under an argon stream, 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) 5.0 g (11.2 mmol), 9-phenanthreneboronic acid 2.62 g (11.8 mmol) ) And 259 mg (0.224 mmol) of tetrakis (triphenylphosphine) palladium were added to 110 mL of THF, and 7.48 mL of 3M-potassium carbonate aqueous solution was further added, and the mixture was heated to reflux for 22 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized from 70 mL of toluene to obtain the desired 2- [3-chloro-5- (9-phenanthryl) phenyl] -4-phenylbenzo [h] quinazoline (C-1) gray powder (yield) 5.26 g, 86% yield).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.56-7.62 (m, 4H), 7.64-7.74 (m, 4H), 7.75-7.83 (m, 4H), 7.89-8.00 (m, 6H), 8.77 (d, J = 8.4 Hz, 1H), 8.82 (d, J = 8.0 Hz, 1H), 8.89 ( t, J = 1.2 Hz, 1H), 8.94 (t, J = 1.6 Hz, 1H), 9.48 (dd, J = 7.6 Hz, 1.6 Hz, 1H).
Under an argon stream, 1.00 g (1.84 mmol) of 2- [3-chloro-5- (9-phenanthryl) phenyl] -4-phenylbenzo [h] quinazoline (C-1), 5- (4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2-phenylpyridine 569 mg (2.02 mmol), palladium acetate 8.3 mg (0.037 mmol), and 2-dicyclohexylphosphino-2 ', 4', 6'-Triisopropylbiphenyl (52.6 mg, 0.110 mmol) was added to THF (35 mL), 3M-potassium carbonate aqueous solution (1.2 mL) was added, and the mixture was heated to reflux for 16 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 200 mL of toluene to obtain the desired 2- [3- (9-phenanthryl) -5- (6-phenylpyridin-3-yl) phenyl] -4-phenylbenzo [h] quinazoline. A white powder of (C-2) (yield 872 mg, yield 72%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.45 (t, J = 7.3 Hz, 1H), 7.52 (t, J = 8.0 Hz, 2H), 7.57-7. 63 (m, 4H), 7.67 (t, J = 7.3 Hz, 1H), 7.72 (t, J = 7.7 Hz, 2H), 7.78-7.84 (m, 3H), 7.88-8.02 (m, 8H), 8.09 (t, J = 8.7 Hz, 3H), 8, 20 (dd, J = 7.7 Hz, 2.3 Hz, 1H), 8.79 (D, J = 8.0 Hz, 1H), 8.84 (d, J = 8.0 Hz, 1H), 9.05 (t, J = 1.6 Hz, 1H), 9.23 (d, J = 1.9 Hz, 1H), 9.26 (t, J = 1.5 Hz, 1H), 9.52 (dd, J = 7.3 Hz, 2.3 Hz, 1H).
Experimental Example-6 (Example)

Under an argon stream, 2- [3-chloro-5- (9-phenanthryl) phenyl] -4-phenylbenzo [h] quinazoline (C-1) 1.00 g (1.84 mmol), 4-biphenylboronic acid 401 mg ( 2.03 mmol), 8.4 mg (0.037 mmol) of palladium acetate, and 35.7 mg (0.074 mmol) of 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl were added to 37 mL of THF. 1.2 mL of 3M potassium carbonate aqueous solution was added and heated to reflux for 38 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized twice with 200 mL of toluene to obtain the desired 2- [5- (9-phenanthryl) -1,1 ′: 4 ′, 1 ″ -terphenyl-3-yl] -4. -A white powder of phenylbenzo [h] quinazoline (C-3) (yield 673 mg, yield 55%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.37 (t, J = 7.3 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.56-7. 63 (m, 4H), 7.64-7.83 (m, 10H), 7.92-8.02 (m, 9H), 8.09 (d, J = 8.2 Hz, 1H), 8. 79 (d, J = 8.2 Hz, 1H), 8.84 (d, J = 8.5 Hz, 1H), 9.00 (t, J = 1.5 Hz, 1H), 9.23 (t, J = 1.8 Hz, 1H), 9.53 (dd, J = 6.4 Hz, 1.7 Hz, 1H).
Experiment-7 (Example)

Under an argon stream, 2- [3-chloro-5- (9-phenanthryl) phenyl] -4-phenylbenzo [h] quinazoline (C-1) 820 mg (1.51 mmol), 3-pyridineboronic acid 223 mg (1. 81 mmol), 6.8 mg (0.030 mmol) of palladium acetate, and 43.1 mg (0.091 mmol) of 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl were added to 30 mL of THF, and 3M- A potassium carbonate aqueous solution (1.0 mL) was added, and the mixture was heated to reflux for 38 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 15 mL of toluene to obtain the desired 2- [3- (9-phenanthryl) -5- (3-pyridyl) phenyl] -4-phenylbenzo [h] quinazoline (C-4). Of white powder (yield 689 mg, 78% yield).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.44 (dd, J = 7.9 Hz, 4.8 Hz, 1H), 7.56-7.62 (m, 4H), 7.65 ( t, J = 7.1 Hz, 1H), 7.69-7.74 (m, 2H), 7.75-7.83 (m, 3H), 7.90-7.94 (m, 5H), 7.97 (t, J = 7.7 Hz, 1H), 8.00 (d, J = 9.0 Hz, 1H), 8.04 (d, J = 8.2 Hz, 1H), 8.13 (dt , J = 8.2 Hz, 1.8 Hz, 1H), 8.65 (dd, J = 4.8 Hz, 1.8 Hz, 1H), 8.78 (d, J = 8.1 Hz, 1H), 8. 83 (d, J = 8.4 Hz, 1H), 9.05 (t, J = 1.6 Hz, 1H), 9.12 (d, J = 1.6 Hz, 1H), 9.18 (t, J = 1.6Hz, 1H , 9.50 (dd, J = 7.1Hz, 2.4Hz, 1H).
Experimental Example-8 (Example)

Under an argon stream, 2- [3-chloro-5- (9-phenanthryl) phenyl] -4-phenylbenzo [h] quinazoline (C-1) 1.50 g (2.76 mmol), bis (vinacolato) diboron 912 mg ( 3.59 mmol), 51 mg (0.055 mmol) of bis (dibenzylideneacetone) palladium, 53 mg (0.110 mmol) of 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, and 542 mg (5 of potassium acetate) .52 mmol) was added to 50 mL of THF and heated to reflux for 20 hours. After allowing to cool to room temperature, water is added and the precipitated solid is collected by filtration and then washed with water, methanol and hexane to give the desired 2- [3- (4,4,5,5-tetramethyl- Gray powder of 1,3,2-dioxaborolan-2-yl) -5- (9-phenanthryl) phenyl] -4-phenylbenzo [h] quinazoline (D-1) (yield 1.28 g, 73% yield) Got.

¹ H-NMR (CDCl ₃ ), δ (ppm): 1.14 (s, 12H), 7.52-7.61 (m, 4H), 7.64 (t, J = 7.6 Hz, 1H) 7.67-7.72 (m, 2H), 7.73-7.81 (m, 3H), 7.84 (s, 1H), 7.90-7.99 (m, 6H), 8 .13 (t, J = 1.5 Hz, 1H), 8.76 (d, J = 8.3 Hz, 1H), 8.81 (d, J = 8.0 Hz, 1H), 9.08 (t, J = 1.8 Hz, 1H), 9.29 (t, J = 1.5 Hz, 1H), 9.52 (dd, J = 6.8 Hz, 2.0 Hz, 1H).
2- [3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5- (9-phenanthryl) phenyl] -4-phenylbenzo [h ] Quinazoline (D-1) 1.00 g (1.58 mmol), 3-bromo-2,6-dimethylpyridine 323 mg (1.73 mmol), and tetrakis (triphenylphosphine) palladium 36.5 mg (0.035 mmol) in THF In addition to 32 mL, 1.1 mL of 3M-potassium carbonate aqueous solution was further added, and the mixture was heated to reflux for 40 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was washed with 50 mL of a mixed solvent of hexane: chloroform = 9: 1 to obtain the desired 2- [3- (2,6-dimethylpyridin-3-yl) -5- (9-phenanthryl) phenyl. ] -4-Phenylbenzo [h] quinazoline (D-2) was obtained as a white powder (yield 809 mg, 84%).

¹ H-NMR (CDCl ₃ ), δ (ppm): 2.62 (s, 3H), 2.70 (s, 3H), 7.13 (d, J = 7.7 Hz, 1H), 7.56 -7.60 (m, 4H), 7.63-7.77 (m, 6H), 7.77-7.82 (m, 2H), 7.89-7.93 (m4H), 7.96 (D, J = 7.7 Hz, 1H), 8.00 (d, J = 9.3 Hz, 1H), 8.06 (d, J = 8.4 Hz, 1H), 8.77 (d, J = 8.0 Hz, 1H), 8.83 (d, J = 8.0 Hz, 1H), 8.89 (t, J = 1.9 Hz, 1H), 9.00 (t, J = 1.9 Hz, 1H) ), 9.47 (d, J = 7.7 Hz, 1H).
Experimental example-9 (Example)

Under an argon stream, 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) 8.44 g (18.9 mmol), phenylboronic acid 2.42 g (19.9 mmol), Then, 97.1 mg (0.379 mmol) of tetrakis (triphenylphosphine) palladium was added to 189 mL of THF, and 12.6 mL of 3M-potassium carbonate aqueous solution was further added, and the mixture was heated to reflux for 24 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 100 mL of toluene to give the desired 2- (5-chlorobiphenyl-3-yl) -4-phenylbenzo [h] quinazoline (E-1) gray powder (yield 7.54 g, Yield 90%).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.43 (t, J = 7.5 Hz, 1H), 7.54 (t, J = 7.5 Hz, 2H), 7.59-7. 66 (m, 3H), 7.72-7.76 (m, 3H), 7.81-7.85 (m, 3H), 7.90-7.96 (m, 3H), 7.99 ( d, J = 9.0 Hz, 1H), 8.80 (t, J = 1.9 Hz, 1H), 8.95 (t, J = 1.5 Hz, 1H), 9.54 (d, J = 9 .0Hz, 1H).
Under an argon stream, 2- [5-chlorobiphenyl-3-yl] -4-phenylbenzo [h] quinazoline (E-1) 7.54 g (17.0 mmol), 4- (4,6-diphenylpyridine-2) -Yl) phenylboronic acid 6.58 g (18.7 mmol), palladium acetate 76.0 mg (0.340 mmol), and 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl 324 mg (0.681 mmol) ) Was added to 340 mL of THF, and further 11.3 mL of 3M aqueous potassium carbonate solution was added, and the mixture was heated to reflux for 24 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized twice with 100 mL of toluene to obtain the desired 4-phenyl-2- [4- (4,6-diphenylpyridin-2-yl) -1,1 ′: 3 ′, 1 ′. A white powder (yield 11.6 g, yield 96%) of '-terphenyl-5'-yl] -benzo [h] quinazoline (E-2) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.44-7.50 (m, 2H), 7.51-7.59 (m, 7H), 7.61-7.67 (m, 3H), 7.79-7.87 (m, 7H), 7.93-8.02 (m, 8H), 8.05 (t, J = 1.8 Hz, 1H), 8.26 (dd, J = 8.3 Hz, 1.4 Hz, 2H), 8, 39 (d, J = 8.4 Hz, 2H), 9.09 (t, J = 1.6 Hz, 1H), 9.15 (t, J = 1.6 Hz, 1H), 9.60 (dd, J = 7.0 Hz, 2.4 Hz, 1H).
Experimental Example-10 (Example)

Under an argon stream, 2- [5-chlorobiphenyl-3-yl] -4-phenylbenzo [h] quinazoline (E-1) 3.66 g (8.26 mmol), bis (vinacolato) diboron 2.73 g (10. 7 mmol), 151 mg (0.165 mmol) bis (dibenzylideneacetone) palladium, 158 mg (0.331 mmol) 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, and 1.62 g (16 0.5 mmol) was added to 165 mL of THF, and the mixture was heated to reflux for 17 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with a mixed solvent of 100 mL of toluene and 100 mL of methanol to obtain the target 2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl. ) A gray powder (yield 3.87 g, 88% yield) of biphenyl-3-yl] -4-phenylbenzo [h] quinazoline (F-1) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 1.40 (s, 12H), 7.38 (t, J = 7.3 Hz, 1H), 7.49 (t, J = 7.6 Hz, 2H), 7.56-7.64 (m, 3H), 7.77-7.85 (m, 5H), 7.89-7.92 (m, 3H), 7.95 (d, J = 8.9 Hz, 1 H), 8.18 (t, J = 1.3 Hz, 1 H), 9.14-9.16 (m, 2 H), 9.58 (dd, J = 7.0 Hz, 2.2 Hz , 1H).
2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) biphenyl-3-yl] -4-phenylbenzo [h] quinazoline (F -1) 1.00 g (1.87 mmol), 2- (4-chlorophenyl) -5-phenylpyridine 547 mg (2.06 mmol), palladium acetate 8.4 mg (0.037 mmol), and 2-dicyclohexylphosphino-2 ', 4', 6'-Triisopropylbiphenyl (35.7 mg, 0.075 mmol) was added to THF (37 mL), 3M-potassium carbonate aqueous solution (1.3 mL) was added, and the mixture was heated to reflux for 24 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized from 200 mL of toluene to obtain the desired 4-phenyl-2- [4- (5-phenylpyridin-2-yl) -1,1 ′: 3 ′, 1 ″ -terphenyl A white powder of -5′-yl] benzo [h] quinazoline (F-2) (yield 953 mg, yield 80%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.42-7.46 (m, 2H), 7.50-7.57 (m, 4H), 7.61-7.69 (m, 5H), 7.82-7.87 (m, 5H), 7.92 (d, J = 8.3 Hz, 1H), 7.94-8.04 (m, 8H), 8.23 (d, J = 8.3 Hz, 2H), 8,99 (d, J = 2.3 Hz, 1H), 9.08 (t, J = 1.7 Hz, 1H), 9.14 (t, J = 1.8 Hz) , 1H), 9.58 (dd, J = 7.4 Hz, 2.9 Hz, 1H).
Experimental Example-11 (Example)

2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) biphenyl-3-yl] -4-phenylbenzo [h] quinazoline (F -1) 1.00 g (1.87 mmol), 2- (4-chlorophenyl) -6-phenylpyridine 547 mg (2.06 mmol), palladium acetate 8.4 mg (0.037 mmol), and 2-dicyclohexylphosphino-2 ', 4', 6'-Triisopropylbiphenyl (35.7 mg, 0.075 mmol) was added to THF (37 mL), 3M-potassium carbonate aqueous solution (1.3 mL) was further added, and the mixture was heated to reflux for 24 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform: hexane = 1: 1) to obtain the desired 4-phenyl-2- [4- (6-phenylpyridin-2-yl) -1, 1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] benzo [h] quinazoline (F-3) was obtained as a white powder (yield 943 mg, yield 79%).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.43-7.47 (m, 2H), 7.54 (dt, J = 8.3 Hz, 4H), 7.61-7.67 ( m, 3H), 7.73 (d, J = 7.5 Hz, 1H), 7.79-7.89 (m, 7H), 7.94-8.04 (m, 7H), 8.20 ( d, J = 7.2 Hz, 2H), 8, 33 (d, J = 7.9 Hz, 2H), 9.08 (t, J = 1.5 Hz, 1H), 9.14 (t, J = 1) .5 Hz, 1 H), 9.59 (dd, J = 5.9 Hz, 2.3 Hz, 1 H).
Experimental example-12 (Example)

Under an argon stream, 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) 10.0 g (22.4 mmol), 4-biphenylboronic acid 5.33 g (26.9 mmol) ) And 518 mg (0.449 mmol) of tetrakis (triphenylphosphine) palladium were added to 449 mL of THF, and further 15.0 mL of 3M potassium carbonate aqueous solution was added, and the mixture was heated to reflux for 32 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized twice with 800 mL of toluene to obtain the desired 2- [5-chloro-1,1 ′: 4 ′, 1 ″ -terphenyl-3-yl] -4-phenylbenzo [h A gray powder of quinazoline (G-1) (yield 9.72 g, yield 83%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.39 (t, J = 7.3 Hz, 1H), 7.49 (t, J = 7.8 Hz, 2H), 7.63 (d, J = 6.8 Hz, 3H), 7.68 (d, J = 7.0 Hz, 2H), 7.75-7.78 (m, 3H), 7.82-7.86 (m, 5H), 7.87-7.92 (m, 3H), 8.00 (d, J = 9.1 Hz, 1H), 8.82 (t, J = 1.8 Hz, 1H), 9.0 (t, J = 1.6 Hz, 1H), 9.55 (d, J = 9.4 Hz, 1H).
Under an argon stream, 2- [5-chloro-1,1 ′: 4 ′, 1 ″ -terphenyl-3-yl] -4-phenylbenzo [h] quinazoline (G-1) 894 mg (1.72 mmol) , 508 mg (1.81 mmol), 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2-phenylpyridine, 8.7 mg (0.038 mmol) palladium acetate, 36.8 mg (0.078 mmol) of 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl was added to 34 mL of THF, and further 1.3 mL of 3M potassium carbonate aqueous solution was added, and the mixture was heated to reflux for 48 hours. did. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 50 mL of toluene to obtain the desired 4-phenyl-2- [5- (6-phenylpyridin-3-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl. A white powder of -3-yl] benzo [h] quinazoline (G-2) (yield 820 mg, yield 75%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.40 (t, J = 7.2 Hz, 1H), 7.44-7.56 (m, 5H), 7.61-7.68 ( m, 3H), 7.71 (d, J = 7.1 Hz, 2H), 7.79 (d, J = 8.7 Hz, 2H), 7.82-7.87 (m, 3H), 7. 91-7.98 (m, 6H), 8, 02 (d, J = 9.0 Hz, 1H), 8.05 (t, J = 1.5 Hz, 1H), 8.11 (d, J = 6 .8 Hz, 2H), 8.21 (dd, J = 8.3 Hz, 2.3 Hz, 1H), 9.14 (t, J = 1.5 Hz, 1H), 8.17 (t, J = 1. 5 Hz, 1H), 9.21 (d, J = 1.9 Hz, 1H), 9.59 (dd, J = 6.8 Hz, 2.6 Hz, 1H).
Experimental Example-13 (Example)

Under an argon stream, 2- [5-chloro-1,1 ′: 4 ′, 1 ″ -terphenyl-3-yl] -4-phenylbenzo [h] quinazoline (G-1) 5.50 g (10. 6 mmol), bis (binacolato) diboron 3.50 g (13.8 mmol), bis (dibenzylideneacetone) palladium 194 mg (0.212 mmol), 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl 202 mg (0.424 mmol) and 2.08 g (21.2 mmol) of potassium acetate were added to 212 mL of THF, and the mixture was heated to reflux for 46 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 150 mL of toluene to obtain the desired 2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,1 ′. : A gray powder of 4 ′, 1 ″ -terphenyl-3-yl] -4-phenylbenzo [h] quinazoline (H-1) (yield: 5.63 g, yield: 87%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.38 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.9 Hz, 2H), 7.60-7. 67 (m, 3H), 7.69 (d, J = 7.1 Hz, 2H), 7.74 (d, J = 8.5 Hz, 2H), 8.80-8.86 (m, 3H), 7.90 (d, J = 8.5 Hz, 2H), 7.94 (d, J = 8.0 Hz, 3H), 7.98 (d, J = 9.0 Hz, 1H), 8.25 (d , J = 2.0 Hz, 1H), 9.19 (t, J = 1.7 Hz, 1H), 9.22 (t, J = 1.7 Hz, 1H), 9.61 (d, J = 7. 1 Hz, 1 H).
2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl-3 under an argon stream -Yl] -4-phenylbenzo [h] quinazoline (H-1) 1.00 g (1.64 mmol), 4- (4-chlorophenyl) isoquinoline 432 mg (1.80 mmol), palladium acetate 7.4 mg (0.033 mmol) ) And 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (31.3 mg, 0.066 mmol) was added to 33 mL of THF, and 1.1 mL of 3M-potassium carbonate aqueous solution was further added for 19 hours. Heated to reflux. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 100 mL of toluene to obtain the desired 4-phenyl-2- [4- (4-isoquinolyl) -1,1 ′: 3 ′, 1 ″: 4 ″, 1 ″. A white powder (yield 793 mg, yield 70%) of “-quaterphenyl-5′-yl] benzo [h] quinazoline (H-2) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.39 (t, J = 7.4 Hz, 1H), 7.50 (t, J = 7.8 Hz, 2H), 7.60-7. 76 (m, 9H), 7.79 (d, J = 8.6 Hz, 2H), 7.83-7.89 (m, 3H), 7.95-7.98 (m, 5H), 8. 00-8.03 (m, 3H), 8,08 (t, J = 6.8 Hz, 2H), 8.11 (t, J = 1.8 Hz, 1H), 8.61 (s, 1H), 9.16 (dd, J = 1.7 Hz, 0.86 Hz, 2H), 9.30 (s, 1H), 9.61 (dd, J = 6.4 Hz, 2.6 Hz, 1H).
Experimental Example-14 (Example)

2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl-3 under an argon stream -Yl] -4-phenylbenzo [h] quinazoline (H-1) 1.00 g (1.64 mmol), 8- (4-chlorophenyl) quinoline 432 mg (1.80 mmol), palladium acetate 7.4 mg (0.033 mmol) ) And 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (31.3 mg, 0.066 mmol) were added to THF (33 mL), and further 3 M-potassium carbonate aqueous solution (1.1 mL) was added for 19 hours. Heated to reflux. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 100 mL of toluene to obtain the desired 4-phenyl-2- [4- (8-quinolyl) -1,1 ′: 3 ′, 1 ″: 4 ″, 1 ″. A white powder (yield 770 mg, yield 68%) of “-quaterphenyl-5′-yl] benzo [h] quinazoline (H-3) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.39 (t, J = 7.3 Hz, 1H), 7.45-7.53 (m, 3H), 7.63-7.73 ( m, 6H), 7.80 (td, J = 8.6 Hz, 2.9 Hz, 2H), 7.85-7.92 (m, 7H), 7.93-8.00 (m, 7H), 8.02 (dd, J = 8.8 Hz, 2.9 Hz, 1H), 8, 11 (dt, J = 2.8 Hz, 1.8 Hz, 1H), 8.25 (dt, J = 8.7 Hz, 2.5Hz, 1H), 9.04 (dt, J = 4.2Hz, 9.2Hz, J = 2.3Hz, 1H), 9.13 (dt, J = 2.8Hz, 1.8Hz, 1H) 9.19 (dt, J = 2.8 Hz, 1.6 Hz, 1H), 9.63 (dt, J = 7.0 Hz, 2.1 Hz, 1H).
Experimental Example-15 (Example)

2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl-3 under an argon stream -Yl] -4-phenylbenzo [h] quinazoline (H-1) 1.00 g (1.64 mmol), 2-chloro-5-phenylpyridine 342 mg (1.80 mmol), palladium acetate 7.4 mg (0.033 mmol) And 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (31.3 mg, 0.066 mmol) are added to 33 mL of THF, and 1.1 mL of 3M potassium carbonate aqueous solution is further added for 48 hours. Heated to reflux. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 30 mL of toluene to obtain the desired 4-phenyl-2- [5- (5-phenylpyridin-2-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl. A white powder of -3-yl] benzo [h] quinazoline (H-4) was obtained (yield 476 mg, yield 45%).

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.40 (t, J = 7.4 Hz, 1H), 7.45 (t, J = 7.3 Hz, 1H), 7.52 (td, J = 8.1 Hz, 4H), 7.62-7.68 (m, 3H), 7.70-7.73 (m, 4H), 7.78-7.80 (d, J = 8.4 Hz) , 2H), 7.82-7.87 (m, 3H), 7.96-7.99 (m, 5H), 8.01 (d, J = 9.3 Hz, 1H), 8.05-8 .13 (m, 2H), 8.58 (t, J = 1.9 Hz, 1H), 9.05 (d, J = 2.4 Hz, 1H), 9.21 (t, J = 1.3 Hz, 1H), 9.44 (t, J = 1.4 Hz, 1H), 9.62 (dd, J = 6.8 Hz, 2.5 Hz, 1H).
Experimental Example-16 (Example)

2- [5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl-3 under an argon stream -Yl] -4-phenylbenzo [h] quinazoline (H-1) 1.00 g (1.64 mmol), 2-bromo-6-phenylpyridine 552 mg (1.97 mmol), and tetrakis (triphenylphosphine) palladium 38 0.0 mg (0.033 mmol) was added to 33 mL of THF, and 1.1 mL of 3M aqueous potassium carbonate solution was further added, and the mixture was heated to reflux for 37 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized with 450 mL of toluene to obtain the desired 4-phenyl-2- [5- (6-phenylpyridin-2-yl) -1,1 ′: 4 ′, 1 ″ -terphenyl. A white powder of -3-yl] benzo [h] quinazoline (H-5) (yield 906 mg, yield 87%) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.39 (tt, J = 7.3 Hz, 1.2 Hz, 1H), 7.45-7.52 (m, 3H), 7.55 ( t, J = 7.2 Hz, 2H), 7.62-7.68 (m, 3H), 7.71 (dd, J = 8.3 Hz, 1.5 Hz, 2H), 7.79-7.87. (M, 6H), 7.93 (t, J = 7.5 Hz, 1H), 7.96-8.00 (m, 6H), 8.03 (d, J = 9.2 Hz, 1H), 8 .28 (dd, J = 8.6 Hz, 1.5 Hz, 2H), 8.66 (t, 1.8 Hz, 1H), 9.19 (t, J = 1.8 Hz, 1H), 9.61 ( t, J = 1.8 Hz, 1H), 9.64 (dd, J = 7.2 Hz, 2.3 Hz, 1H).
Experimental Example-17 (Example)

Under an argon stream, 2- (3-bromo-5-chlorophenyl) -4-phenylbenzo [h] quinazoline (A-3) 5.0 g (11.2 mmol), 4-biphenylboronic acid 4.89 g (24.7 mmol) ), 50.4 mg (0.224 mmol) of palladium acetate, and 214 mg (0.449 mmol) of 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl were added to 200 mL of THF, and further 3M-potassium carbonate aqueous solution. 15.0 mL was added and heated to reflux for 72 hours. After allowing to cool to room temperature, water was added and the precipitated solid was collected by filtration and then washed with water, methanol, and hexane. The obtained solid was recrystallized twice with 800 mL of toluene to obtain the desired 2- (1,1 ′: 4 ′, 1 ″: 3 ″, 1 ′ ″: 4 ′ ″, 1 ″. A white powder (yield 6.23 g, yield 87%) of “-kinkphenyl-5” -yl) -4-phenylbenzo [h] quinazoline (H-6) was obtained.

¹ H-NMR (CDCl ₃ ), δ (ppm): 7.38 (t, J = 7.3 Hz, 2H), 7.50 (t, J = 7.3 Hz, 3H), 7.60-7. 65 (m, 4H), 7.67-7.69 (t, J = 8.6 Hz, 3H), 7.74-7.79 (m, 4H), 7.82-7.86 (m, 6H) ), 7.92-8.02 (m, 6H), 8.81 (t, J = 1.8 Hz, 1H), 9.00 (t, J = 1.5 Hz, 1H), 9.11 (d , J = 1.8 Hz, 1H), 9.55 (dd, J = 5.9 Hz, 2.9 Hz, 1H).
Experimental Example-18 (Example)

Under an argon stream, 2-aminobenzophenone 500 mg (2.54 mmol), 3,5-dibromobenzaldehyde 669 mg (2.54 mmol), and ammonium acetate 448 mg (6.34 mmol) were dissolved in ethanol 1.3 mL, and iodine 32 mg (0 .127 mmol) was added, followed by heating and stirring at 70 ° C. for 19 hours. After cooling to room temperature, 5 ml of water was added, and the precipitated solid was collected by filtration. The obtained solid was washed with water and methanol to obtain the desired 2- (3,5-dibromophenyl) -4-phenylquinazoline (I-1) white solid (yield 686 mg, 61%).

¹ H-NMR (CDCl ₃ ): 7.59-7.64 (m, 4H), 7.79 (s, 1H), 7.86-7.89 (m, 2H), 7.93 (t, J = 7.6 Hz, 1H), 8.16 (dd, J = 4.2 Hz, 3.5 Hz, 2H), 8.80 (d, J = 1.8 Hz, 2H).
Experimental Example-19 (Example)

Under an argon stream, 2- (3,5-dibromophenyl) -4-phenylquinazoline (I-1) 742 mg (1.69 mmol), 4- (2-pyridyl) phenylboronic acid 738 mg (3.71 mmol), palladium acetate 7.6 mg (0.0337 mmol) and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (32 mg, 0.0674 mmol) were added to dioxane (56 mL), and 3M-potassium carbonate aqueous solution (3.4 mL) was further added. The mixture was added and stirred at 80 ° C. overnight. After cooling to room temperature, water was added and the precipitated solid was collected by filtration and washed with water, methanol, and hexane. The obtained solid was recrystallized from toluene to obtain the desired 4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5 ′. A white solid (yield 649 mg, 65% yield) of -yl] quinazoline (I-2) was obtained.

¹ H-NMR (CDCl ₃ ): 7.24-7.28 (m, 2H), 7.57-7.64 (m, 4H), 7.77-7.84 (m, 4H), 7. 90-7.95 (m, 7H), 8.07 (s, 1H), 8.15-8.19 (m, 5H), 8.23 (d, J = 8.4 Hz, 1H), 8. 74 (d, J = 4.5 Hz, 2H), 9.02 (d, J = 1.7 Hz, 2H).
Experimental Example-20 (Example)

Under an argon stream, 2.00 g (8.63 mmol) of 2-amino-5-chlorobenzophenone, 2.28 g (8.63 mmol) of 3,5-dibromobenzaldehyde, and 1.66 g (21.58 mmol) of ammonium acetate were added to ethanol. After dissolving in 3 mL and adding 109 mg (0.432 mmol) of iodine, it was heated and stirred at 70 ° C. for 24 hours. After cooling to room temperature, 10 mL of water was added, and the precipitated solid was collected by filtration. The obtained solid was washed with water and methanol, and the desired 2- (3,5-dibromophenyl) -6-chloro-4-phenylquinazoline (J-1) white solid (yield 1.91 g, yield 47). %).

¹ H-NMR (CDCl ₃ ): 7.64 (t, J = 3.1 Hz, 3H), 7.80 (t, J = 1.9 Hz, 1H), 7.84-7.88 (m, 3H) ), 8.10 (d, J = 5.8 Hz, 1H), 8.12 (s, 1H), 8.77 (d, J = 1.7 Hz, 2H).
Experimental Example-21 (Example)

Under an argon stream, 2- (3,5-dibromophenyl) -6-chloro-4-phenylquinazoline (J-1) 1.91 g (4.02 mmol), 4- (2-pyridyl) phenylboronic acid 1.76 g (8.84 mmol) and 92.9 mg (0.0804 mmol) of tetrakis (triphenylphosphine) palladium were added to 80 mL of THF, and 5.4 mL of 3M-potassium carbonate aqueous solution was further added, followed by heating and refluxing overnight. After cooling to room temperature, water was added and the precipitated solid was collected by filtration and washed with water, methanol, and hexane. The obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain the desired 6-chloro-4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′. : 3 ′, 1 ″ -terphenyl-5′-yl] quinazoline (J-2) was obtained as a white solid (yield 1.41 g, yield 56%).

¹ H-NMR (CDCl ₃ ): 7.27 (dd, J = 4.7 Hz, 1.7 Hz, 1H), 7.64-7.67 (m, 3H), 7.77-7.84 (m , 4H), 7.86 (dd, J = 9.1 Hz, 2.3 Hz, 1H), 7.90-7.94 (m, 6H), 8.07 (t, J = 1.7 Hz, 1H) 8.14-8.19 (m, 7H), 8.74 (dt, J = 4.8 Hz, 1.4 Hz, 2H), 8.99 (d, J = 1.7 Hz, 2H).
Under a stream of argon, 6-chloro-4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] quinazoline ( J-2) 1.41 g (2.26 mmol), phenylboronic acid 331 mg (2.72 mmol), palladium acetate 10.1 mg (0.0452 mmol), and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′- 33.1 mg (0.0904 mmol) of triisopropylbiphenyl was added to 45 mL of THF, and 1.5 mL of 3M-potassium carbonate aqueous solution was further added, and the mixture was heated to reflux for 5.5 hours. After cooling to room temperature, water was added and the precipitated solid was collected by filtration and washed with water, methanol, and hexane. The obtained solid was recrystallized with 100 mL of toluene to obtain the desired 4,6-diphenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″- A white solid of terphenyl-5′-yl] quinazoline (J-3) (yield 1.21 g, yield 81%) was obtained.

¹ H-NMR (CDCl ₃ ): 7.28 (dd, J = 4.7 Hz, 1.3 Hz, 2H), 7.41 (tt, J = 7.6 Hz, 1.2 Hz, 1H), 7.50 (T, J = 7.6 Hz, 2H), 7.62-7.68 (m, 5H), 7.77-7.85 (m, 4H), 7.95 (d, J = 8.6 Hz, 4H), 7.97-8.00 (m, 2H), 8.08 (t, J = 1.8 Hz, 1H), 8.16 (d, J = 8.5 Hz, 4H), 8.19 ( dd, J = 8.7 Hz, 2.0 Hz, 1H), 8.30 (d, J = 8.7 Hz, 1H), 8.34 (d, J = 1.7 Hz, 1H), 8.74 (dt , J = 4.7 Hz, 1.5 Hz, 2H), 9.03 (d, J = 1.7 Hz, 2H).
Test Example-1 (Example)
Preparation and evaluation of the organic electroluminescent element were performed as follows. As the substrate, a glass substrate with an ITO transparent electrode in which an indium-tin oxide (ITO) film having a width of 2 mm was patterned in a stripe shape was used. The substrate was cleaned with isopropyl alcohol and then surface-treated by oxygen plasma cleaning. Each layer was vacuum-deposited on the cleaned substrate by a vacuum evaporation method, and an organic electroluminescence device having a light-emitting area of 4 mm ² as shown in FIG.

First, the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 × 10 ⁻⁴ Pa. Thereafter, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4 and an electron transport layer 5 are sequentially formed as an organic compound layer on the glass substrate indicated by 1 in FIG. Filmed.

As the hole injection layer 2, sublimation-purified HIL was vacuum-deposited with a film thickness of 65 nm.

As the hole transport layer 3, HAT and HTL were vacuum-deposited with a thickness of 5 nm and 10 nm, respectively.

As the light-emitting layer 4, EML-1 and EML-2 were vacuum-deposited at a thickness of 25 nm at a ratio of 954: 46 (mass%).

As the electron transport layer 5, 4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ − obtained in Experimental Example-3 of the present invention was used. Terphenyl-5′-yl] benzo [h] quinazoline (A-4) was vacuum deposited to a thickness of 30 nm.
Finally, a metal mask was disposed so as to be orthogonal to the ITO stripe, and the cathode layer 6 was formed. As the cathode layer 6, Liq, silver magnesium, and silver were vacuum-deposited with a thickness of 0.5 nm, 80 nm, and 20 nm, respectively, to form a three-layer structure.

Each organic material was formed into a film by a resistance heating method, and the heated compound was vacuum-deposited at a film formation rate of 0.6 to 3.0 nm / second.

Each film thickness was measured with a stylus type film thickness meter (DEKTAK). Furthermore, this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less. For the sealing, a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used. The structural formulas and abbreviations of the compounds used are shown below.

A direct current was applied to the produced organic electroluminescence device, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON. As light emission characteristics, voltage (V), luminance (cd / m ² ), current efficiency (cd / A), and power efficiency (lm / W) when a current density of 10 mA / cm ² was passed were measured.

Test Example-2 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 4-phenyl-2- [5- (1-pyrenyl) -4 ′-(2-pyridyl) biphenyl-3-yl obtained in Experimental Example 4 instead of benzo [h] quinazoline (A-4) An organic electroluminescent device was produced in the same manner as in Test Example 1 except that benzo [h] quinazoline (B-2) was used, and evaluated in the same manner as in Test Example-1.

Test Example 3 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 In place of benzo [h] quinazoline (A-4), 2- [3- (9-phenanthryl) -5- (6-phenylpyridin-3-yl) phenyl] -4- obtained in Experimental Example-5 An organic electroluminescent element was produced in the same manner as in Test Example 1 except that phenylbenzo [h] quinazoline (C-2) was used, and evaluated in the same manner as in Test Example-1.

Test Example 4 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 2- [3- (9-phenanthryl) -5- (3-pyridyl) phenyl] -4-phenylbenzo [h] obtained in Experimental Example-7 An organic electroluminescent device was produced in the same manner as in Test Example 1 except that quinazoline (C-4) was used, and evaluated in the same manner as in Test Example-1.

Test Example-5 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 4-phenyl-2- [4- (4,6-diphenylpyridin-2-yl) -1,1 ′ obtained in Experimental Example-9 in place of benzo [h] quinazoline (A-4): 3 An organic electroluminescent device was prepared in the same manner as in Test Example 1 except that “, 1 ″ -terphenyl-5′-yl] -benzo [h] quinazoline (E-2) was used. Evaluation was performed in the same manner as in 1.

Test Example-6 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [4- (5-phenylpyridin-2-yl) -1,1 ′: 3 ′ obtained in Experimental Example-10 An organic electroluminescent device was prepared in the same manner as in Test Example 1 except that 1 ″ -terphenyl-5′-yl] benzo [h] quinazoline (F-2) was used, and the same as in Test Example-1. Evaluated.

Test Example-7 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [4- (6-phenylpyridin-2-yl) -1,1 ′ obtained in Experimental Example-11, 3 ′, An organic electroluminescent device was produced in the same manner as in Test Example 1 except that 1 ″ -terphenyl-5′-yl] benzo [h] quinazoline (F-3) was used, and the same as in Test Example-1. Evaluated.

Test Example-8 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [5- (6-phenylpyridin-3-yl) -1,1 ′ obtained in Experimental Example-12, 4 ′, An organic electroluminescent device was prepared in the same manner as in Test Example 1 except that 1 ″ -terphenyl-3-yl] benzo [h] quinazoline (G-2) was used. evaluated.

Test Example-9 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [4- (4-isoquinolyl) -1,1 ′: 3 ′, 1 ″: 4 obtained in Experimental Example-13 ”, 1 ′ ″-Quaterphenyl-5′-yl] benzo [h] quinazoline (H-2) was used, and an organic electroluminescence device was prepared and tested in the same manner as in Test Example 1. Evaluation was performed in the same manner as in Example-1.

Test Example-10 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [4- (8-quinolyl) -1,1 ′: 3 ′, 1 ″: 4 obtained in Experimental Example-14 ”, 1 ′ ″-Quaterphenyl-5′-yl] benzo [h] quinazoline (H-3) was used, and an organic electroluminescent device was prepared and tested in the same manner as in Test Example-1. Evaluation was performed in the same manner as in Example-1.

Test Example-11 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [5- (5-phenylpyridin-2-yl) -1,1 ′: 4 ′ obtained in Experimental Example-15 An organic electroluminescent device was prepared in the same manner as in Test Example 1 except that 1 ″ -terphenyl-3-yl] benzo [h] quinazoline (H-4) was used. evaluated.

Test Example-12 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 2- (1,1 ′: 4 ′, 1 ″: 3 ″, 1 ′ ″: 4 ′ ″ obtained in Experimental Example-17 , 1 ″ ″-kinkphenyl-5 ″ -yl) -4-phenylbenzo [h] quinazoline (H-6) was used to produce an organic electroluminescent device in the same manner as in Test Example-1. Then, evaluation was made in the same manner as in Test Example-1.

Test Example-13 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′ obtained in Experimental Example-19 An organic electroluminescent device was produced in the same manner as in Test Example 1 except that 1 ″ -terphenyl-5′-yl] quinazoline (I-2) was used, and evaluated in the same manner as in Test Example-1.

Test Example-14 (Example)
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 4,6-diphenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′ obtained in Experimental Example-21 in place of benzo [h] quinazoline (A-4): 3 An organic electroluminescent device was produced in the same manner as in Test Example 1 except that “, 1 ″ -terphenyl-5′-yl] quinazoline (J-3) was used, and evaluated in the same manner as in Test Example-1. did.

Reference Example-1
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), 2,4-diphenyl-6- [4,4 ″ -di (2-pyridyl) -1,1 ′: 3 described in Patent No. WO2008 / 129912 An organic electroluminescent device obtained by vacuum-depositing ', 1''-terphenyl-5'-yl] -1,3,5-triazine (represented by the following formula) was prepared and measured in the same manner as in Test Example-1. did.

Comparative Example-1
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 An organic electroluminescent device obtained by vacuum-depositing 2,4-diphenylbenzoquinazoline (represented by the following formula) described in Patent No. WO2006 / 104118 instead of benzo [h] quinazoline (A-4) 1 was prepared and measured in the same manner.

Comparative Example-2
4-phenyl-2- [4,4 ″ -bis (2-pyridyl) -1,1 ′: 3 ′, 1 ″ -terphenyl-5′-yl] of the electron transport layer 5 of Test Example-1 Instead of benzo [h] quinazoline (A-4), an organic electroluminescent device in which 2,4-diphenylquinazoline (represented by the following formula) contained in Patent No. WO2006 / 104118 was vacuum-deposited was tested in Test Example 1. It produced and measured similarly.

The measurement results of Test Examples-1 to 14, Reference Example-1, and Comparative Examples-1 and 2 are summarized in the table below.

Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

Note that Japanese Patent Application No. 2014-1111639 filed on May 29, 2014, Japanese Patent Application No. 2014-124117 filed on June 17, 2014, and Japanese Patent Application No. 2014-124117 filed on June 18, 2014. The entire contents of the specification, claims, drawings, and abstract of Japanese Patent Application No. 2014-125801 are incorporated herein by reference as the disclosure of the specification of the present invention.

The thin film comprising the compound (1) of the present invention exhibits high thin film stability, heat resistance, electron transport properties, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection properties, etc. Especially as a material of an electroluminescent element, it can use suitably as an electron transport material. The compound (1) of the present invention has a wide energy gap and triplet energy, and can be used in combination with a fluorescent or phosphorescent organic electroluminescent material. Moreover, the compound (1) of this invention can be used for a light emission host layer other than an electron carrying layer from the characteristic. Moreover, it can be used even if it mixes or laminates with another compound as an electron carrying layer. Furthermore, this compound has high solubility, and can be used for coating elements in addition to vapor deposition. From these effects, these elements are expected to have significant effects such as suppression of battery consumption by reducing power consumption, improvement of product life by extending life, and reduction of burden on the drive circuit.

1. 1. Glass substrate with ITO transparent electrode 2. hole injection layer Hole transport layer 4. 4. Light emitting layer Electron transport layer 6. Cathode layer

Claims (20)

1. A compound represented by the general formula (1).
   

   

   (In the formula, Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a benzene ring and / or pyridine) Aromatic groups consisting only of 6 to 6 rings in which 2 to 6 rings are connected and / or condensed {These groups include a methyl group, a methoxy group, a fluorine atom, a pyrimidyl group (the pyrimidyl group is a methyl group, a carbon number 2-10 alkyl groups and at least one substituent selected from the group consisting of C6-C18 aromatic hydrocarbon groups), or a C2-C10 alkyl group, alkoxy A group, an alkoxyalkyl group, an ester group or an esteralkyl which may be substituted}.
   A represents the general formula (2-1), the general formula (2-2), or the general formula (2-3).
   

   

   Of the formulas (2-1), (2-2), and (2-3),
   * Represents a linking site.
   Ar ³ , Ar ⁴ and Ar ⁵ are each an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom, alkyl group having 2 to 10 carbon atoms, alkoxy group, And may be substituted with an alkoxyalkyl group, an ester group or an ester alkyl group).
   Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a methyl group, a methoxy group, a fluorine atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms (methyl group, methoxy group, pyridyl group, pyrimidyl group, fluorine atom) Or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group.
   R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ , and R ³² are each independently a hydrogen atom Represents a methyl group, a methoxy group, a phenyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group.
   In addition, each hydrogen atom in the formula may independently be a deuterium atom. )
2. Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 6 benzene rings and / or pyridine rings. An aromatic group consisting of only six linked and / or condensed six-membered rings {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, Or a pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group). The compound according to claim 1, which may be substituted.
3. Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 5 benzene rings and / or pyridine rings. An aromatic group consisting of only six linked and / or condensed six-membered rings {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, Or a pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group). The compound according to claim 1, which may be substituted.
4. Ar ¹ and Ar ² are each independently a phenyl group, a pyridyl group, a pyrimidyl group, a pyrimidyl group substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or 2 to 4 benzene rings and / or pyridine rings. An aromatic group consisting of only six linked and / or condensed six-membered rings {these groups are a methyl group, a methoxy group, an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 10 carbon atoms, a fluorine atom, Or a pyrimidyl group (the pyrimidyl group may have at least one substituent selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, and a pyrenyl group). The compound according to claim 1, which may be substituted.
5. Ar ³ , Ar ⁴ and Ar ⁵ are aromatic hydrocarbon groups having 6 to 12 carbon atoms (the group is a methyl group, a methoxy group, an alkyl or alkoxy group having 2 to 10 carbon atoms, a pyridyl group, a pyrimidyl group, The compound according to claim 1, which may be substituted with a fluorine atom.
6. Ar ³ , Ar ⁴ and Ar ⁵ are a phenyl group, a naphthyl group, or a biphenyl group (these groups are a methyl group, a methoxy group, a pyridyl group, a pyrimidyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms, an alkoxy group) The compound according to claim 1, which may be substituted with a group, an alkoxyalkyl group, an ester group or an esteralkyl group.
7. The compound according to claim 1, wherein Ar ³ , Ar ⁴ and Ar ⁵ are a phenyl group, a naphthyl group or a biphenyl group.
8. The compound according to claim 1, wherein Ar ³ , Ar ⁴ and Ar ⁵ are phenyl groups.
9. R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ³¹ , and R ³² are hydrogen atoms 1. The compound according to 1.
10. Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a methyl group, a methoxy group, a fluorine atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms (the group is a methyl group, methoxy group, 2 to The compound according to claim 1, which may be substituted with a 10 alkyl group, an alkoxy group having 2 to 10 carbon atoms, a pyridyl group, a pyrimidyl group, or a fluorine atom.
11. Ar ⁶ and Ar ⁷ are each independently a phenyl group, a naphthyl group, or a biphenyl group (these substituents are a methyl group, a methoxy group, a pyridyl group, a pyrimidyl group, a fluorine atom, or an alkyl group having 2 to 10 carbon atoms) Or an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group), a hydrogen atom, a methyl group, a methoxy group, or a fluorine atom.
12. The compound according to claim 1, wherein Ar ⁶ and Ar ⁷ are each independently a hydrogen atom, a phenyl group, a naphthyl group, or a biphenyl group.
13. The compound according to claim 1, wherein Ar ⁶ and Ar ⁷ are each independently a hydrogen atom or a phenyl group.
14. In the presence of a metal catalyst or in the presence of a metal catalyst and a base, the compound represented by the general formula (3), the compound represented by the general formula (4), and the compound represented by the general formula (5) are one step. Alternatively, the method for producing the compound according to claim 1, wherein the coupling reaction is performed in two steps.
    

    

    (A, Ar ¹ , and Ar ^{2 in} formulas (1), (3), (4), and (5) are the same as in claim 1. Z ¹ and Z ² are each independently a leaving group. And M ¹ and M ² each independently represent a metal group, a boronic acid group, or a boronic ester group.)
15. The compound according to claim 14, which is represented by the general formula (3-1), the general formula (3-2), or the general formula (3-3).
    

    

    (The definition of each symbol in the formula is the same as in claim 14.)
16. In the presence of a catalyst, in the presence of an acid, in the presence of a base, in the presence of a catalyst and an acid, or in the presence of a catalyst and a base and in the presence or absence of a nitrogen source, The compound represented by formula (7-1) is cyclized with the compound represented by formula (7-1), or the compound represented by formula (6-2) and the formula (7-2) 16. The compound according to claim 15, wherein the compound is cyclized or the compound represented by the general formula (6-3) and the compound represented by the general formula (7-3) are cyclized. A method for producing a compound represented by formula (3-1), formula (3-2), or formula (3-3).
    

    

    (Formulas (3-1), (3-2), (3-3), (6-1), (6-2), (6-3), (7-1), (7-2), In (7-3), W ¹¹ , W ¹² , W ¹³ , W ²¹ , W ²² , W ²³ , W ³¹ , W ³² and W ³³ represent substituents necessary for carrying out the pyrimidine ring formation reaction. For all other symbols, those defined in claims 1 and 15 are the same.)
17. The compound represented by the general formula (9-1) or the general formula (9-2) is present in the presence of an oxidizing agent in the presence or absence of an acid, or in the presence or absence of a base. A process for producing a benzoquinazoline compound represented by the general formula (3-1) or the general formula (3-2) according to claim 15,
    

    

    (The definitions of the symbols in formulas (3-1), (3-2), (9-1), and (9-2) are the same as in claim 15).
18. The material for organic electroluminescent elements containing the compound of Claim 1.
19. A light emitting layer host material, an electron injection material or an electron transport material comprising the compound according to claim 1.
20. An electron injection material or an electron transport material comprising the compound according to claim 1.

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