JP2006241053A - 1,10-phenanthroline derivative, method for producing the same and organic electroluminescent device comprising the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a 1,10-phenanthroline derivative, to provide a method for producing the derivative and to provide an organic electroluminescent device comprising the same compound. <P>SOLUTION: The 1,10-phenanthroline derivative is represented by general formula (1). The method for producing the derivative and the organic electroluminescent element comprising the derivative are provided. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a novel heterocyclic compound that can be used for a light emitting element that emits light by converting electric energy into light and various organic semiconductor devices, that is, a 1,10-phenanthroline derivative, a method for producing the same, and an organic material containing the same. The present invention relates to an electroluminescent element.

  In recent years, various organic compounds have been found to have various functions, and research on using them as display element materials, memory materials and the like has been actively conducted. Among these, organic electroluminescence elements (organic EL elements; organic electroluminescence elements) are particularly attracting attention because they can emit light with a relatively low voltage and high luminance. As a typical example, a light-emitting element composed of an organic thin film formed by vapor deposition of an organic compound is well known (Non-Patent Document 1). This light-emitting element has a structure in which tris (8-hydroxyquinolinato) aluminum (Alq3), which is an electron transporting / light-emitting material, and (triarylamine compound), which is a hole-transporting material, are stacked, The light emission characteristics are significantly improved as compared with the device.

  However, there are still many problems to be solved such as stability, durability, light emission luminance, light emission efficiency, and voltage reduction of the organic electroluminescence device in practical use. As a technique for improving the luminance and luminous efficiency, for example, a method of doping a tris (8-hydroxyquinolinato) aluminum (Alq3) layer with a fluorescent dye such as a coumarin derivative is known. By this method, light of a desired color can be emitted by selecting a dye to be doped. However, if the drive voltage is increased in order to obtain high luminance, light emission from Alq3 is mixed, resulting in a problem that the color purity is lowered. In addition, there is known a technique for improving luminous efficiency by using an electron transport material having hole blocking properties such as bathophenanthroline and bathocuproin (BCP) which are one of 1,10-phenanthroline derivatives. However, a problem with the light-emitting elements using is that the elements are significantly deteriorated during high temperature storage and continuous light emission. The cause of this deterioration is presumably because the crystallinity of the material is very good and the glass transition point (Tg) is low.

  On the other hand, with regard to lowering the driving voltage of the organic electroluminescent device, there is a method for facilitating electron injection by providing a cathode interface layer such as lithium fluoride between the cathode and the electron transport layer. Are known. In addition, a method for lowering the voltage by doping sodium into an electron transport layer made of bathophenanthroline, which is one of 1,10-phenanthroline derivatives, has recently been reported (Non-patent Document 2). However, from the viewpoint of practical use of the organic electroluminescent device, it is necessary to further reduce the driving voltage.

また、１，１０−フェナントロリン誘導体を発光素子等に使用した例としては、１，１０−フェナントロリン骨格の特定の位置に置換基を有する化合物を電子輸送層に用いた有機電界発光素子（特許文献１〜８）および１，１０−フェナントロリン骨格を２〜３つ有する化合物を電子輸送層に用いた有機電界発光素子（特許文献９）が開示されているが、その電子輸送性能は不十分であった。 For 1,10-phenanthroline derivatives, various synthetic methods as described below have already been reported.

In addition, as an example of using a 1,10-phenanthroline derivative in a light emitting element or the like, an organic electroluminescent element using a compound having a substituent at a specific position of a 1,10-phenanthroline skeleton in an electron transporting layer (Patent Document 1) -8) and an organic electroluminescent device (Patent Document 9) using a compound having two or three 1,10-phenanthroline skeletons as an electron transport layer has been disclosed, but its electron transport performance was insufficient. .

Appl. Phys. Lett. 51, 913 (1987). Appl. Phys. Lett. 73, 2866 (1998). J. et al. Org. Chem. 61, 3017 (1996). Tetrahedron, 36, 10685 (1994). J. et al. Am. Chem. Soc. 68, 1320 (1946). J. et al. Am. Chem. Soc. , 66, 396 (1944). JP-A-5-331459 Japanese Patent Laid-Open No. 7-82551 Japanese Patent Laid-Open No. 10-79297 JP 2001-267080 A JP 2001-131174 A JP 2004-107263 A JP 2004-175691 A JP 2004-311184 A JP 2003-115387 A

  An object of the present invention is to provide a novel 1,10-phenanthroline derivative, a production method thereof, and an organic electroluminescence device containing the compound.

  As a result of diligent research aimed at solving the above problems, the present inventors discovered for the first time that a specific compound having a 1,10-phenanthroline structure has extremely high electron transport performance, and thus completed the present invention. It is a thing.

（式中、Ｒ^１〜Ｒ^１２は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数１〜２０のアルキル基、炭素数１〜２０のパーフルオロアルキル基、置換もしくは無置換の炭素数３〜２０のアルケニル基、置換もしくは無置換の炭素数６〜４５のアリール基、置換もしくは無置換の炭素数４〜４０のヘテロアリール基、炭素数３〜４０の有機ケイ素基、置換もしくは無置換の炭素数１〜２０のアルコキシ基、置換もしくは無置換の炭素数６〜２０のアリールオキシ基、置換もしくは無置換の炭素数２〜３０のジアルキルアミノ基、置換もしくは無置換の炭素数１２〜４０のジアリールアミノ基、置換もしくは無置換の炭素数１０〜４０のアリールヘテロアリールアミノ基、置換もしくは無置換の炭素数７〜４０のアルキルアリールアミノ基、置換もしくは無置換の炭素数５〜４０のアルキルヘテロアリールアミノ基よりなる群からそれぞれ独立して選ばれた基であり；Ｒ^１〜Ｒ^１２は、それぞれ隣接した置換基同士で結合して環状構造を形成しても良い。）
で示される１，１０−フェナントロリン誘導体に関する。
本発明の第２は、下記一般式（２）

（式中、Ｒ^７〜Ｒ^１１は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数１〜２０のアルキル基、炭素数１〜２０のパーフルオロアルキル基、置換もしくは無置換の炭素数３〜２０のアルケニル基、置換もしくは無置換の炭素数６〜４５のアリール基、置換もしくは無置換の炭素数４〜４０のヘテロアリール基、炭素数３〜４０の有機ケイ素基、置換もしくは無置換の炭素数１〜２０のアルコキシ基、置換もしくは無置換の炭素数６〜２０のアリールオキシ基、置換もしくは無置換の炭素数２〜３０のジアルキルアミノ基、置換もしくは無置換の炭素数１２〜４０のジアリールアミノ基、置換もしくは無置換の炭素数１０〜４０のアリールヘテロアリールアミノ基、置換もしくは無置換の炭素数７〜４０のアルキルアリールアミノ基、置換もしくは無置換の炭素数５〜４０のアルキルヘテロアリールアミノ基よりなる群からそれぞれ独立して選ばれた基であり；Ｒ^１２は、水素原子、置換もしくは無置換の炭素数１〜２０のアルキル基、炭素数１〜２０のパーフルオロアルキル基、置換もしくは無置換の炭素数３〜２０のアルケニル基、置換もしくは無置換の炭素数６〜４５のアリール基、置換もしくは無置換の炭素数４〜４０のヘテロアリール基、炭素数３〜４０の有機ケイ素基、置換もしくは無置換の炭素数１〜２０のアルコキシ基、置換もしくは無置換の炭素数６〜２０のアリールオキシ基、置換もしくは無置換の炭素数２〜３０のジアルキルアミノ基、置換もしくは無置換の炭素数１２〜４０のジアリールアミノ基、置換もしくは無置換の炭素数１０〜４０のアリールヘテロアリールアミノ基、置換もしくは無置換の炭素数７〜４０のアルキルアリールアミノ基、置換もしくは無置換の炭素数５〜４０のアルキルヘテロアリールアミノ基よりなる群から選ばれた基であり；Ｒ^７〜Ｒ^１２は、それぞれ隣接した置換基同士で結合して環状構造を形成しても良い。）
で示されるアミノ誘導体と下記一般式（３）

（式中、Ｒ^１〜Ｒ^６は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数１〜２０のアルキル基、炭素数１〜２０のパーフルオロアルキル基、置換もしくは無置換の炭素数３〜２０のアルケニル基、置換もしくは無置換の炭素数６〜４５のアリール基、置換もしくは無置換の炭素数４〜４０のヘテロアリール基、炭素数３〜４０の有機ケイ素基、置換もしくは無置換の炭素数１〜２０のアルコキシ基、置換もしくは無置換の炭素数６〜２０のアリールオキシ基、置換もしくは無置換の炭素数２〜３０のジアルキルアミノ基、置換もしくは無置換の炭素数１２〜４０のジアリールアミノ基、置換もしくは無置換の炭素数１０〜４０のアリールヘテロアリールアミノ基、置換もしくは無置換の炭素数７〜４０のアルキルアリールアミノ基、置換もしくは無置換の炭素数５〜４０のアルキルヘテロアリールアミノ基よりなる群からそれぞれ独立して選ばれた基であり；Ｒ^１〜Ｒ^６は、それぞれ隣接した置換基同士で結合して環状構造を形成しても良い。）
で示されるα−メチレンカルボニル化合物とを反応させることを特徴とする
下記一般式（１）

（式中、Ｒ^１〜Ｒ^１２は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数１〜２０のアルキル基、炭素数１〜２０のパーフルオロアルキル基、置換もしくは無置換の炭素数３〜２０のアルケニル基、置換もしくは無置換の炭素数６〜４５のアリール基、置換もしくは無置換の炭素数４〜４０のヘテロアリール基、炭素数３〜４０の有機ケイ素基、置換もしくは無置換の炭素数１〜２０のアルコキシ基、置換もしくは無置換の炭素数６〜２０のアリールオキシ基、置換もしくは無置換の炭素数２〜３０のジアルキルアミノ基、置換もしくは無置換の炭素数１２〜４０のジアリールアミノ基、置換もしくは無置換の炭素数１０〜４０のアリールヘテロアリールアミノ基、置換もしくは無置換の炭素数７〜４０のアルキルアリールアミノ基、置換もしくは無置換の炭素数５〜４０のアルキルヘテロアリールアミノ基よりなる群からそれぞれ独立して選ばれた基であり；Ｒ^１〜Ｒ^１２ は、それぞれ隣接した置換基同士で結合して環状構造を形成しても良い。）
で示される請求項１記載の１，１０−フェナントロリン誘導体の製法に関する。
本発明の第３は、一般式（１）で表わされる１，１０−フェナントロリン誘導体よりなる電子輸送材料に関する。
本発明の第４は、一般式（１）で表わされる１，１０−フェナントロリン誘導体よりなる電子注入材料に関する。
本発明の第５は、一般式（１）で表わされる１，１０−フェナントロリン誘導体よりなる発光材料に関する。
本発明の第６は、一対の電極間に一般式（１）で表わされる１，１０−フェナントロリン誘導体を少なくとも一種含有する層を含む有機電界発光素子に関する。
本発明の第７は、一般式（１）で表される１，１０−フェナントロリン誘導体を含有する層が、電子輸送層である請求項６記載の有機電界発光素子に関する。
本発明の第８は、一般式（１）で表される１，１０−フェナントロリン誘導体を含有する層が、電子注入層である請求項６記載の有機電界発光素子に関する。
本発明の第９は、一般式（１）で表わされる１，１０−フェナントロリン誘導体を含有する層が、発光層である請求項６記載の有機電界発光素子に関する。
本発明の第１０は、一般式（１）で示される１，１０−フェナントロリン誘導体を含有する層にアルカリ金属がドーピングされている請求項６記載の有機電界発光素子に関する。
本発明の第１１は、アルカリ金属がドーピングされている一般式（１）で表される１，１０−フェナントロリン誘導体を含有する層が、電子輸送層である請求項１０記載の有機電界発光素子に関する。
本発明の第１２は、アルカリ金属がドーピングされている一般式（１）で表される１，１０−フェナントロリン誘導体を含有する層が、電子注入層である請求項１０記載の有機電界発光素子に関する。 The first of the present invention is the following general formula (1)

(Wherein R ^{1 to} R ¹² are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group) An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 To 40 diarylamino groups, substituted or unsubstituted arylheteroarylamino groups having 10 to 40 carbon atoms, substituted or unsubstituted alkylaryl groups having 7 to 40 carbon atoms Arylamino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹ to R ¹² are bonded with a substituent group among adjacent respectively To form a ring structure.)
And a 1,10-phenanthroline derivative represented by:
The second of the present invention is the following general formula (2)

Wherein R ^{7 to} R ¹¹ are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 To 40 diarylamino groups, substituted or unsubstituted arylheteroarylamino groups having 10 to 40 carbon atoms, substituted or unsubstituted alkylaryl groups having 7 to 40 carbon atoms Arylamino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹² represents a hydrogen atom, a substituted or unsubstituted 1 to carbon atoms 20 alkyl groups, perfluoroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 45 carbon atoms, substituted or unsubstituted carbons A heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, substituted or An unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, a substituted or unsubstituted carbon number 10 A group selected from the group consisting of 40 arylheteroarylamino groups, substituted or unsubstituted alkylarylamino groups having 7 to 40 carbon atoms, and substituted or unsubstituted alkylheteroarylamino groups having 5 to 40 carbon atoms R ^{7 to} R ¹² may be bonded to each other with adjacent substituents to form a cyclic structure.
And an amino derivative represented by the following general formula (3)

(In the formula, R ^{1 to} R ⁶ are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 -40 diarylamino group, substituted or unsubstituted arylheteroarylamino group having 10 to 40 carbon atoms, substituted or unsubstituted alkyl aryl having 7 to 40 carbon atoms Amino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹ to R ⁶ are bonded with a substituent group among adjacent respectively To form a ring structure.)
A reaction with an α-methylenecarbonyl compound represented by the following general formula (1):

(Wherein R ^{1 to} R ¹² are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group) An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 To 40 diarylamino groups, substituted or unsubstituted arylheteroarylamino groups having 10 to 40 carbon atoms, substituted or unsubstituted alkylaryl groups having 7 to 40 carbon atoms Arylamino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹ to R ¹² are bonded with a substituent group among adjacent respectively To form a ring structure.)
The manufacturing method of the 1,10-phenanthroline derivative of Claim 1 shown by these.
The third of the present invention relates to an electron transport material comprising a 1,10-phenanthroline derivative represented by the general formula (1).
The fourth of the present invention relates to an electron injection material comprising a 1,10-phenanthroline derivative represented by the general formula (1).
5th of this invention is related with the luminescent material which consists of a 1,10-phenanthroline derivative represented by General formula (1).
The sixth aspect of the present invention relates to an organic electroluminescence device including a layer containing at least one 1,10-phenanthroline derivative represented by the general formula (1) between a pair of electrodes.
7th of this invention is related with the organic electroluminescent element of Claim 6 whose layer containing the 1, 10- phenanthroline derivative represented by General formula (1) is an electron carrying layer.
An eighth aspect of the present invention relates to the organic electroluminescent device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is an electron injection layer.
The ninth of the present invention relates to the organic electroluminescence device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is a light emitting layer.
The tenth aspect of the present invention relates to the organic electroluminescent device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is doped with an alkali metal.
The eleventh aspect of the present invention relates to the organic electroluminescent device according to claim 10, wherein the layer containing a 1,10-phenanthroline derivative represented by the general formula (1) doped with an alkali metal is an electron transport layer. .
The twelfth aspect of the present invention relates to the organic electroluminescence device according to claim 10, wherein the layer containing a 1,10-phenanthroline derivative represented by the general formula (1) doped with an alkali metal is an electron injection layer. .

  As the halogen atom, any of fluorine, chlorine, bromine and iodine can be used.

  Examples of the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms include methyl group, methoxymethyl group, benzyloxymethyl group, cyanomethyl group, dimethylaminomethyl group, diethylaminomethyl group, dibutylaminomethyl group, ethyl group, 2- Methoxyethyl group, 2- (2-methoxyethoxy) ethyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2- (dimethylamino) ethyl group, 2- (dibutylamino) ethyl group, n-propyl group, Isopropyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3- (dimethylamino) propyl group, n-butyl group, 2-butyl group, tert-butyl group, n-pentyl group, 2-pentyl group, 3 -Pentyl group, neopentyl group, n-hexyl group, 2-hexyl group, 2-ethylhexyl group, 2-butylhexyl Sill group, n- heptyl, n- octyl, 2-octyl, n- nonyl, n- decyl group, n- dodecyl group.

  Examples of the perfluoroalkyl group having 1 to 20 carbon atoms include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorohexyl group, perfluorocyclohexyl group, and perfluoro. Examples include heptyl group, perfluorooctyl group, perfluorononyl group, perfluorodecyl group, perfluorododecyl group, perfluorotridecyl group, perfluorotetradecyl group, perfluoropentadecyl group and the like.

  Examples of the substituted or unsubstituted alkenyl group having 3 to 20 carbon atoms include allyl group, 1-propenyl group, 2-methylpropenyl group, 1-butenyl group, 3-methyl-2-butenyl group, styryl group, 4-methoxy group. Styryl group, 4- (trifluoromethyl) styryl group, 4-phenylstyryl group, 4-cyanostyryl group, 2- (1-naphthyl) vinyl group, 2- (9-anthryl) vinyl group, 2,2-diphenyl A vinyl group, 4-phenyl-1,3-butadienyl group, etc. are mentioned.

  Examples of the substituted or unsubstituted aryl group having 6 to 45 carbon atoms include phenyl group, 1-naphthyl group, 2-naphthyl group, 4-phenyl-1-naphthyl group, 1-anthryl group, 2-anthryl group, 9- Anthryl group, 10-phenyl-9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-pyrenyl group, 2-pyrenyl group, 2-perenylenyl Group, 3-perylenyl group, 1-fluoranthenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 2-triphenylenyl group, 9,9-dimethylfluoren-2-yl Group, 9,9-dibutylfluoren-2-yl group, 9,9-dihexylfluoren-2-yl group, 9,9-dioctylfluorene 2-yl group, 9,9-diphenylfluoren-2-yl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-3-yl group, p-terphenyl-4-yl Group, m-terphenyl-3-yl group, m-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-4-yl group, 4- (1-naphthyl)- 1-naphthyl group, o-tolyl group, m-tolyl group, p-tolyl group, p-tert-butylphenyl group, 4-methoxyphenyl group, 4-fluorophenyl group, 4-dimethylaminophenyl group, 4-cyano Phenyl, 4-trifluorophenyl, 4-methyl-1-naphthyl, 4-phenyl-1-naphthyl, 2-methoxy-1-naphthyl, 10-methyl-9-anthryl, 10-meth Ci-9-anthryl group, 4-phenyl-8-fluoranthenyl group, 7-dimethylamino-9,9-dimethylfluoren-2-yl group, 3 ', 5'-diphenylbiphenyl-4-yl group, benzyl Group, 4-methoxybenzyl group, 4-fluorobenzyl group, 3- (dimethylamino) benzyl group, 4-phenylbenzyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, 1- (2-methoxynaphthyl) methyl Group, 9-anthrylmethyl group, diphenylmethyl group, di (p-tolyl) methyl group, di (4-methoxyphenyl) methyl group, di (1-naphthyl) methyl group, trityl group, p-methoxyphenyldiphenylmethyl Group, di (p-methoxyphenyl) phenylmethyl group, tri (p-methoxyphenyl) methyl group, (1-naphthyl) diphenylmethyl Group, phenethyl group, 1-phenylethyl group, 2- (4-methoxyphenyl) ethyl group, 2- (4-fluorophenyl) ethyl group, 2- (4-cyanophenyl) ethyl group, 2- (1-naphthyl) ) Ethyl group, 2- (2-naphthyl) ethyl group, 2- (p-tolyl) ethyl group, 2- (9-anthryl) ethyl group, 2- (4-methoxyphenyl) ethyl group, 3-phenylpropyl group 1-phenylpropyl group, 3- (4-methoxyphenyl) propyl group, 3- (4-fluorophenyl) propyl group, 3- (4-cyanophenyl) propyl group, 3- (1-naphthyl) propyl group, 3- (2-naphthyl) propyl group, 3- (p-tolyl) propyl group, 3- (9-anthryl) propyl group, 3- (4-methoxyphenyl) propyl group, 4-phenylbutyl group, -Phenylbutyl group, 1-phenylbutyl group, 4- (4-methoxyphenyl) butyl group, 4- (1-naphthyl) butyl group, 4- (2-methoxy-1-naphthyl) butyl group, (2-pyridyl) ) Methyl group, (2-quinolyl) methyl group, (2-thienyl) methyl group, (2-quinoxalinyl) methyl group, (2-quinazolinyl) methyl group, (2-phenanthridinyl) methyl group, (9- Acridinyl) methyl group and the like.

Examples of the substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms include 2-furyl group, 4-phenyl-2-furyl group, 2-thienyl group, 4-phenyl-2-thienyl group, 4- (2- Thienyl) -2-thienyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 4-phenyl-2-pyridyl group, 6-phenyl-2-pyridyl group, 4- (dimethylamino) -2- Pyridyl group, 2,2'-bipyridyl-6-yl group, 2,2'-bipyridyl-5-yl group, 2,3'-bipyridyl-6-yl group, 2-pyrimidinyl group, 2-pyrazinyl group, 2 -Indolizinyl group, 2-isoindolyl group, 8-purinyl group, 1-isoquinolyl group, 3-isoquinolyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 8-quinolyl group, 8-methoxy-2-yl group Quinolyl 4-phenyl-2-quinolyl group, 2-quinoxalinyl group, 2-quinazolinyl group, 4-quinazolinyl group, 5-quinazolinyl group, 6-quinazolinyl group, 2-pteridinyl group, 2-carbazolyl group, 3-phenanthridinyl Group, 4-phenanthridinyl group, 6-phenanthridinyl group, 8-phenanthridinyl group, 2-acridinyl group, 3-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-2- Yl group , 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group, 3-phenyl-1,10-phenanthrolin-2-yl group 3-phenyl-1,10-phenanthrolin-4-yl group, 3-phenyl-1,10-phenanthroline-5-yl group, 4- Eniru phenanthroline-2-yl group, 4,7-diphenyl-1,10-phenanthroline-3-yl group, 4-phenyl-1,10-phenanthroline-5-yl group, 4,7-diphenyl -1,10-phenanthrolin-2-yl group, 4-phenyl-1,10-phenanthroline-3-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1 , 8-phenanthroline-4-yl group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9 -Yl group, 1,7-phenanthrolin-2-yl group, 1-phenazinyl group, 2-phenazinyl group, benzo [b] furan-2-yl group, benzo [b Furan-3-yl group, benzo [b] furan-5-yl group, benzo [b] furan-6-yl group, benzo [b] thiophen-2-yl group, benzo [b] thiophen-3-yl group , Benzo [b] thiophen-5-yl group, benzo [b] thiophen-6-yl group, 1-methylindol-2-yl group, 1-methylindol-3-yl group, 1-methylindole-5 Yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, dibenzofuran-4-yl group, dibenzothiophen-1-yl group, dibenzothiophen-2-yl group, dibenzothiophene- 3-yl group, dibenzothiophen-4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazol-3-yl group, 9-methylcarbazol Ru-2-yl group, 9-methylcarbazol-3-yl group, benzo [b] [1,8] naphthyridin-2-yl group, pyrido [2,3-g] quinolin-2-yl group, pyrido [ 3,2-g] quinolin-2-yl group, 1,8,9-triazaanthracen-2-yl group and the like.

  Examples of the organic silicon group having 3 to 40 carbon atoms include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, trihexylsilyl group, dimethylisopropylsilyl group, diethylisopropylsilyl group, and trioctyl group. Silyl group, tridecylsilyl group, tert-butyldimethylsilyl group, tribenzylsilyl group, dimethylphenylsilyl group, diethylphenylsilyl group, dimethyl (p-tolyl) silyl group, dimethyl (m-tolyl) silyl group, dimethyl ( 1-naphthyl) silyl group, dimethyl (2-naphthyl) silyl group, dimethyl (9-anthryl) silyl group, dimethyl (4-methoxyphenyl) silyl group, dimethyl (4-dimethylaminophenyl) silyl group, methyldiphenylsilyl group , Iso Propyl diphenylsilyl group, n-butyldiphenylsilyl group, tert-butyldiphenylsilyl group, methyldi (p-tolyl) silyl group, methyldi (1-naphthyl) silyl group, triphenylsilyl group, tri (p-tolyl) silyl Group, (1-naphthyl) diphenylsilyl group, (2-naphthyl) diphenylsilyl group, diphenyl (p-tolyl) silyl group, (4-methoxyphenyl) diphenylsilyl group and the like.

  Examples of the substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms include methoxy group, ethoxy group, 2-methoxyethyloxy group, 2- (2-methoxyethoxy) ethyloxy group, 2-ethoxyethyloxy group, and 2-butoxy. Ethyloxy group, 2- (dimethylamino) ethyloxy group, 2- (dibutylamino) ethyloxy group, propoxy group, isopropoxy group, 3-methoxypropyloxy group, 3-ethoxypropyloxy group, 3- (dimethylamino) propyl Oxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, isopentyloxy group, 2-pentyloxy group, 3-pentyloxy group, neopentyloxy group, hexyloxy group, 2 -Hexyloxy group, 2-ethylhexyloxy group, 2- Tylhexyloxy group, heptyloxy group, octyloxy group, 2-octyloxy group, nonyloxy group, decyloxy group, dodecyloxy group, allyloxy group, benzyloxy group, 4-methoxybenzyloxy group, 4-fluorobenzyloxy group, 3 -(Dimethylamino) benzyloxy group, 4-phenylbenzyloxy group, 1-naphthylmethyloxy group, 2-naphthylmethyloxy group, 1- (2-methoxynaphthyl) methyloxy group, 9-anthrylmethyloxy group, Diphenylmethyloxy group, di (p-tolyl) methyloxy group, di (4-methoxyphenyl) methyloxy group, di (1-naphthyl) methyloxy group, triphenylmethyloxy group, 3-phenylpropyloxy group, etc. Can be mentioned.

  Examples of the substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-phenyl-1-naphthyloxy group, 1-anthryloxy group, 2 -Anthryloxy group, 9-anthryloxy group, 10-phenyl-9-anthryloxy group, 1-phenanthryloxy group, 2-phenanthryloxy group, 3-phenanthryloxy group, 4- Phenanthryloxy group, 9-phenanthryloxy group, 1-pyrenyloxy group, 2-pyrenyloxy group, 2-perylenyloxy group, 3-perylenyloxy group, 1-fluoranthenyloxy group, 2-fluoranthenyloxy group, 3-fluoranthenyloxy group, 8-fluoranthenyloxy group, 2-triphenylenyloxy group, 9,9-dimethyl Luolen-2-yloxy group, 9,9-dibutylfluoren-2-yloxy group, 9,9-dihexylfluoren-2-yloxy group, 9,9-dioctylfluoren-2-yloxy group, 9,9-diphenylfluorene- 2-yloxy group, 2-biphenylyloxy group, 3-biphenylyloxy group, 4-biphenylyloxy group, p-terphenyl-3-yloxy group, p-terphenyl-4-yloxy group, m-terphenyl -3-yloxy group, m-terphenyl-4-yloxy group, o-terphenyl-3-yloxy group, o-terphenyl-4-yloxy group, 4- (1-naphthyl) -1-naphthyloxy group, o-tolyloxy group, m-tolyloxy group, p-tolyloxy group, p-tert-butylphenyloxy group, 4-methoxy Phenyloxy group, 4-fluorophenyloxy group, 4-dimethylaminophenyloxy group, 4-cyanophenyloxy group, 4-trifluorophenyloxy group, 4-methyl-1-naphthyloxy group, 4-phenyl-1- Naphthyloxy group, 2-methoxy-1-naphthyloxy group, 10-methyl-9-anthryloxy group, 10-methoxy-9-anthryloxy group, 4-phenyl-8-fluoranthenyloxy group, 7- Dimethylamino-9,9-dimethylfluoren-2-yloxy group, 4-phenyl-2-furyloxy group, 2-thienyloxy group, 4-phenyl-2-thienyloxy group, 4- (2-thienyl) -2 -Thienyloxy group, 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group, 4-phenyl-2-pyridy Ruoxy group, 6-phenyl-2-pyridyloxy group, 4- (dimethylamino) -2-pyridyloxy group, 2-pyrimidinyloxy group, 2-pyrazinyloxy group, 2-indolidinyloxy group, 2-isoindolyl Oxy group, 8-prynyloxy group, 1-isoquinolyloxy group, 3-isoquinolyloxy group, 2-quinolyloxy group, 3-quinolyloxy group, 4-quinolyloxy group, 8-quinolyloxy group, 8-methoxy-2-yl group Quinolyloxy group, 4-phenyl-2-quinolyloxy group, 2-quinoxalinyloxy group, 2-quinazolinyloxy group, 4-quinazolinyloxy group, 5-quinazolinyloxy group, 6-quinazolinyl Oxy group, 2-pteridinyloxy group, 2-carbazolyloxy group, 3-phenanthridinyloxy group, 4-phenanthri Nyloxy group, 6-phenanthridinyloxy group, 8-phenanthridinyloxy group, 2-acridinyloxy group, 3-acridinyloxy group, 9-acridinyloxy group, 1,10-phenanthroline -2-yloxy group, 1,10-phenanthroline-4-yloxy group, and the like.

  Examples of the substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms include dimethylamino group, ethylmethylamino group, diethylamino group, methylpropylamino group, isopropylmethylamino group, butylmethylamino group, isobutylmethylamino group, ethyl Propylamino group, dipropylamino group, diisopropylamino group, butylethylamino group, ethylisobutylamino group, dibutylamino group, diisobutylamino group, methylpentylamino group, ethylpentylamino group, hexylmethylamino group, ethylhexylamino group, Butylhexylamino group, hexylpentylamino group, dihexylamino group, dicyclopentylamino group, cyclohexylmethylamino group, cyclohexylethylamino group, cyclohexylisopropylamino group, Cyclohexylamino group, methyloctylamino group, heptylmethylamino group, heptylisopropylamino group, diheptylamino group, methyloctylamino group, octylpropylamino group, dioctylamino group, decylethylamino group, decylisopropylamino group, di ( 2-ethylhexyl) amino group, dodecylmethylamino group, dodecylhexylamino group, cyclohexyldodecylamino group, didodecylamino group and the like.

  Examples of the substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms include diphenylamino group, N, N-di (o-tolyl) amino group, N, N-di (m-tolyl) amino group, N, N -Di (p-tolyl) amino group, N, N-di (1-naphthyl) amino group, N, N-di (2-naphthyl) amino group, N- (1-naphthyl) -N-phenylamino group, N- (4-methoxyphenyl) -N-phenylamino group, N- (4-ethylphenyl) -N-phenylamino group, N- (4-fluorophenyl) -N-phenylamino group, N- (4- Dimethylaminophenyl) -N-phenylamino group, N- (2-naphthyl) -N-phenylamino group, N- (1-naphthyl) -N- (o-tolyl) amino group, N- (2-naphthyl) -N- (o-tolyl) amino group, N- ( -Anthryl) phenylamino group, N- (2-anthryl) -N-phenylamino group, N- (9-anthryl) -N-phenylamino group, N- (10-methyl-9-anthryl) -N-phenyl Amino group, N- (1-anthryl) -N- (1-naphthyl) amino group, N- (2-anthryl) -N- (1-naphthyl) amino group, N- (9-anthryl) -N- ( 2-naphthyl) amino group, N- (10-methyl-9-anthryl) -N- (2-naphthyl) amino group, N- (9-phenanthryl) -N-phenylamino group, N- (9-phenanthryl) -N- (p-tolyl) amino group, N- (1-naphthyl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N-phenylamino group, N- (9,9-dimension Rufluoren-2-yl) -N- (m-tolyl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (1-naphthyl) amino group, N- (9,9-dimethyl) Fluoren-2-yl) -N- (4-methoxyphenyl) amino group, N- (1-anthryl) -N- (9,9-dimethylfluoren-2-yl) amino group, N- (9,9- Dimethylfluoren-2-yl) -N- (9-phenanthryl) amino group, N, N-bis (9,9-dimethylfluoren-2-yl) amino group, N- (3-fluoranthenyl) -N- Phenylamino group, N- (3-fluoranthenyl) -N- (p-tolyl) amino group, N- (3-fluoranthenyl) -N- (4-methoxyphenyl) amino group, N- (3- Fluoranthenyl) -N- (1-naphthyl) a Mino group, N- (3-fluoranthenyl) -N- (2-naphthyl) amino group, N- (1-anthryl) -N- (3-fluoranthenyl) amino group, N- (9-anthryl) -N- (3-fluoranthenyl) amino group, N- (3-fluoranthenyl) -N- (9-phenanthryl) amino group, N- (3-fluoranthenyl) -N- (9,9- Dimethylfluoren-2-yl) amino group, N, N-di (3-fluoranthenyl) amino group, N-phenyl-N- (1-pyrenyl) amino group, N- (1-pyrenyl) -N- ( p-tolyl) amino group, N- (4-dimethylaminophenyl) -N- (1-pyrenyl) amino group, N- (1-naphthyl) -N- (1-pyrenyl) amino group, N- (2- Naphthyl) -N- (1-pyrenyl) amino group, N- (1-ant ) -N- (1-pyrenyl) amino group, N- (9-anthryl) -N- (1-pyrenyl) amino group, N- (1-pyrenyl) -N- (9-phenanthryl) amino group, N -(9,9-dimethylfluoren-2-yl) -N- (1-pyrenyl) amino group, N- (3-fluoranthenyl) -N- (1-pyrenyl) amino group, N- (9-fluro) Olanthenyl) -N- (1-pyrenyl) amino group, N- (3-perylenyl) -N-phenylamino group, N- (3-perylenyl) -N- (m-tolyl) amino group, N- (4 -Dimethylaminomethyl) -N- (3-perylenyl) amino group, N- (1-naphthyl) -N- (3-perylenyl) amino group, N- (2-naphthyl) -N- (3-perylenyl) amino The group N- (1-anthryl) -N- (3-perylenyl) a Group, N- (3-perylenyl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (3-perylenyl) amino group, N- (9 -Fluoranthenyl) -N- (3-perylenyl) amino group, bis (4-dimethylaminophenyl) amino group, bis (4-diphenylaminophenyl) amino group and the like.

Examples of the substituted or unsubstituted arylheteroarylamino group having 10 to 40 carbon atoms include N-phenyl-N- (2-pyridyl) amino group and N- (2-pyridyl) -N- (m-tolyl) amino group. N- (1-naphthyl) -N- (2-pyridyl) amino group, N- (2-naphthyl) -N- (2-pyridyl) amino group, N- (1-anthryl) -N- (2- Pyridyl) amino group, N- (9-phenanthryl) -N- (2-pyridyl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (2-pyridyl) amino group, N- (9-fluoranthenyl) -N- (2-pyridyl) amino group, N- (3-fluoranthenyl) -N- (2-pyridyl) amino group, N- (1-pyrenyl) -N- (2 -Pyridyl) amino group, N- (3-perylenyl) -N- ( -Pyridyl) amino group, N- (benzo [b] furan-2-yl) -N-phenylamino group, N- (benzo [b] furan-2-yl) -N- (m-tolyl) amino group, N- (benzo [b] furan-2-yl) -N- (1-naphthyl) amino group, N- (benzo [b] furan-2-yl) -N- (2-naphthyl) amino group, N- (1-anthryl) -N- (benzo [b] furan-2-yl) amino group, N- (benzo [b] furan-2-yl) -N- (9-phenanthryl) amino group, N- (benzo [B] furan-2-yl) -N- (9,9-dimethylfluoren-2-yl) amino group, N- (benzo [b] furan-2-yl) -N- (9-fluoranthenyl) Amino group, N- (benzo [b] furan-2-yl) -N- (3-fluoranthenyl) a Group, N- (benzo [b] furan-2-yl) -N- (1-pyrenyl) amino group, N- (benzo [b] furan-2-yl) -N- (3-perylenyl) amino group N- (benzo [b] thiophen-2-yl) -N-phenylamino group, N- (benzo [b] thiophen-2-yl) -N- (m-tolyl) amino group, N- (benzo [ b] thiophen-2-yl) -N- (1-naphthyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-naphthyl) amino group, N- (1-anthryl) -N- (benzo [b] thiophen-2-yl) amino group, N- (benzo [b] thiophen-2-yl) -N- (9-phenanthryl) amino group, N- (benzo [b] thiophene- 2-yl) -N- (9,9-dimethylfluoren-2-yl) amino Group, N- (benzo [b] thiophen-2-yl) -N- (9-fluoranthenyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (3-fluoranthenyl) ) Amino group, N- (benzo [b] thiophen-2-yl) -N- (1-pyrenyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (3-perylenyl) amino Group, N- (1-methylindol-2-yl) -N-phenylamino group, N- (1-methylindol-2-yl) -N- (m-tolyl) amino group, N- (1-methyl) Indol-2-yl) -N- (1-naphthyl) amino group, N- (1-methylindol-2-yl) -N- (2-naphthyl) amino group, N- (1-anthryl) -N- (1-methylindol-2-yl) amino group, N- (1-methyl) Indol-2-yl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (1-methylindol-2-yl) amino group, N- ( 9-fluoranthenyl) -N- (1-methylindol-2-yl) amino group, N- (3-fluoranthenyl) -N- (1-methylindol-2-yl) amino group, N- ( 1-methylindol-2-yl) -N- (1-pyrenyl) amino group, N- (1-methylindol-2-yl) -N- (3-perylenyl) amino group, N- (dibenzofuran-3- Yl) -N-phenylamino group, N- (dibenzofuran-3-yl) -N- (m-tolyl) amino group, N- (dibenzofuran-3-yl) -N- (1-naphthyl) amino group, N -(Dibenzofuran-3-yl -N- (2-naphthyl) amino group, N- (1-anthryl) -N- (dibenzofuran-3-yl) amino group, N- (dibenzofuran-3-yl) -N- (9-phenanthryl) amino group N- (dibenzofuran-3-yl) -N- (9,9-dimethylfluoren-2-yl) amino group, N- (dibenzofuran-3-yl) -N- (9-fluoranthenyl) amino group, N- (dibenzofuran-2-yl) -N- (3-fluoranthenyl) amino group, N- (dibenzofuran-3-yl) -N- (1-pyrenyl) amino group, N- (dibenzofuran-3-yl) ) -N- (3-perylenyl) amino group, N- (dibenzofuran-3-yl) -N- (2-pyridyl) amino group, N- (dibenzofuran-3-yl) -N- (2-furyl) amino Group N- (Givet Nzofuran-3-yl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N- (dibenzofuran-3-yl) amino group, N- (dibenzofuran-3- Yl) -N- (benzo [b] thiophen-2-yl) amino group, N- (dibenzofuran-3-yl) -N- (1-methylindol-2-yl) amino group, N, N-di ( Dibenzothiophen-2-yl) amino group, N, N-di (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N-phenylamino group, N- (dibenzothiophene-3) -Yl) -N- (m-tolyl) amino group, N- (dibenzothiophen-3-yl) -N- (1-naphthyl) amino group, N- (dibenzothiophen-3-yl) -N- (2 -Naphthyl) amino group, -(1-anthryl) -N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N- (9-phenanthryl) amino group, N- (dibenzothiophen-3-yl) ) -N- (9,9-dimethylfluoren-2-yl) amino group, N- (dibenzothiophen-3-yl) -N- (9-fluoranthenyl) amino group, N- (dibenzothiophen-2-yl) Yl) -N- (3-fluoranthenyl) amino group, N- (dibenzothiophen-3-yl) -N- (1-pyrenyl) amino group, N- (dibenzothiophen-3-yl) -N- ( 3-perylenyl) amino group, N-phenyl-N- (7-quinolyl) amino group, N- (2-quinolyl) -N- (m-tolyl) amino group, N- (1-naphthyl) -N- ( 2-quinolyl) ami Group, N- (2-naphthyl) -N- (2-quinolyl) amino group, N- (1-anthryl) -N- (2-quinolyl) amino group, N- (9-phenanthryl) -N- (2 -Quinolyl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (2-quinolyl) amino group, N- (9-fluoranthenyl) -N- (2-quinolyl) amino group N- (3-fluoranthenyl) -N- (2-quinolyl) amino group, N- (1-pyrenyl) -N- (2-quinolyl) amino group, N- (3-perylenyl) -N- ( 2-quinolyl) amino group, N- (1-isoquinolyl) -N-phenylamino group, N- (1-isoquinolyl) -N- (m-tolyl) amino group, N- (1-isoquinolyl) -N- ( 1-naphthyl) amino group, N- (1-isoquinolyl) -N- (2-na Butyl) amino group, N- (1-anthryl) -N- (1-isoquinolyl) amino group, N- (1-isoquinolyl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluorene) -2-yl) -N- (1-isoquinolyl) amino group, N- (9-fluoranthenyl) -N- (1-isoquinolyl) amino group, N- (3-fluoranthenyl) -N- (1 -Isoquinolyl) amino group, N- (1-isoquinolyl) -N- (1-pyrenyl) amino group, N- (1-isoquinolyl) -N- (3-perylenyl) amino group, N-phenyl-N- (2 -Quinazolinyl) amino group, N- (2-quinazolinyl) -N- (m-tolyl) amino group, N- (1-naphthyl) -N- (2-quinazolinyl) amino group, N- (2-naphthyl)- N- (2-quinazolinyl) a Group, N- (1-anthryl) -N- (2-quinazolinyl) amino group, N- (9-phenanthryl) -N- (2-quinazolinyl) amino group, N- (9,9-dimethylfluorene-2 -Yl) -N- (2-quinazolinyl) amino group, N- (9-fluoranthenyl) -N- (2-quinazolinyl) amino group, N- (3-fluoranthenyl) -N- (2-quinazolinyl) ) Amino group, N- (1-pyrenyl) -N- (2-quinazolinyl) amino group, N- (3-perylenyl) -N- (2-quinazolinyl) amino group, N-phenyl-N- (2-quinoxalinyl) ) Amino group, N- (2-quinoxalinyl) -N- (m-tolyl) amino group, N- (1-naphthyl) -N- (2-quinoxalinyl) amino group, N- (2-naphthyl) -N- (2-Quinoxalinyl) amino Group, N- (1-anthryl) -N- (2-quinoxalinyl) amino group, N- (9-phenanthryl) -N- (2-quinoxalinyl) amino group, N- (9,9-dimethylfluorene-2- Yl) -N- (2-quinoxalinyl) amino group, N- (9-fluoranthenyl) -N- (2-quinoxalinyl) amino group, N- (3-fluoranthenyl) -N- (2-quinoxalinyl) Amino group, N- (1-pyrenyl) -N- (2-quinoxalinyl) amino group, N- (3-perylenyl) -N- (2-quinoxalinyl) amino group, N- (9-methylcarbazol-2-yl) ) -N-phenylamino group, N- (9-methylcarbazol-2-yl) -N- (m-tolyl) amino group, N- (9-methylcarbazol-2-yl) -N- (1-naphthyl) ) Amino group, N- (9-methylcarbazol-2-yl) -N- (2-naphthyl) amino group, N- (1-anthryl) -N- (9-methylcarbazol-2-yl) amino group, N- (9 -Methylcarbazol-2-yl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (9-methylcarbazol-2-yl) amino group, N -(9-fluoranthenyl) -N- (9-methylcarbazol-2-yl) amino group, N- (3-fluoranthenyl) -N- (9-methylcarbazol-2-yl) amino group, N -(9-methylcarbazol-2-yl) -N- (1-pyrenyl) amino group, N- (9-methylcarbazol-2-yl) -N- (3-perylenyl) amino group, N- (6- Phenanthridinyl) -N-Fe Ruamino group, N- (6-phenanthridinyl) -N- (m-tolyl) amino group, N- (1-naphthyl) -N- (6-phenanthridinyl) amino group, N- (2- Naphthyl) -N- (6-phenanthridinyl) amino group, N- (1-anthryl) -N- (6-phenanthridinyl) amino group, N- (6-phenanthridinyl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (6-phenanthridinyl) amino group, N- (9-fluoranthenyl) -N- (6 -Phenanthridinyl) amino group, N- (3-fluoranthenyl) -N- ( 6-phenanthridinyl) amino group, N- (6-phenanthridinyl ) -N- (1 -pyrenyl) Amino group, N- (3-perylenyl) -N- (6-phenanthridi ) Amino group, N- (9-acridinyl) -N-phenylamino group, N- (9-acridinyl) -N- (m-tolyl) amino group, N- (9-acridinyl) -N- (1- Naphthyl) amino group, N- (9-acridinyl) -N- (2-naphthyl) amino group, N- (9-acridinyl) -N- (1-anthryl) amino group, N- (9-acridinyl) -N -(9-phenanthryl) amino group, N- (9-acridinyl) -N- (9,9-dimethylfluoren-2-yl) amino group, N- (9-acridinyl) -N- (9-fluoranthenyl) ) Amino group, N- (9-acridinyl) -N- (3-fluoranthenyl) amino group, N- (9-acridinyl) -N- (1-pyrenyl) amino group, N- (9-acridinyl)- N- (3-perylenyl) amino Group, N- (1,10-phenanthrolin-2-yl) -N-phenylamino group, N- (1,10-phenanthroline-2-yl) -N- (m-tolyl) amino group, N- (1 -Naphthyl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (2-
Naphthyl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (1-anthryl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (1,10- Phenanthroline-2-yl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (1,10-phenanthroline-2-yl) amino group, N- (9-fluoranthenyl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (3-fluoranthenyl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (1,10-phenanthrolin-2-yl) -N- (1-pyrenyl) amino group, N- (1,10-phenanthroline-2-yl) -N- (3-perylenyl) amino group, N- Phenyl-N- 2-phenazinyl) amino group, N- (2-phenazinyl) -N- (m-tolyl) amino group, N- (1-naphthyl) -N- (2-phenazinyl) amino group, N- (2-naphthyl) -N- (2-phenazinyl) amino group, N- (1-anthryl) -N- (2-phenazinyl) amino group, N- (9-phenanthryl) -N- (2-phenazinyl) amino group, N- ( 9,9-dimethylfluoren-2-yl) -N- (2-phenazinyl) amino group, N- (9-fluoranthenyl) -N- (2-phenazinyl) amino group, N- (3-fluoranthenyl) ) -N- (2-phenazinyl) amino group, N- (2-phenazinyl) -N- (1-pyrenyl) amino group, N- (2-phenazinyl) -N- (3-perylenyl) amino group and the like. It is done.

Examples of the substituted or unsubstituted alkylarylamino group having 7 to 40 carbon atoms include N-methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-phenyl-N-propylamino group, N- Isopropyl-N-phenylamino group, N-butyl-N-phenylamino group, N- (2-butyl) -N-phenylamino group, N-isobutyl-N-phenylamino group, N- (tert-butyl)- N-phenylamino group, N-pentyl-N-phenylamino group, N-hexyl-N-phenylamino group, N-cyclohexyl-N-phenylamino group, N-cyclopentylmethyl-N-phenylamino group, N-heptyl -N-phenylamino group, N-octyl-N-phenylamino group, N-nonyl-N-phenylamino group, N-decyl-N-pheny Amino group, N-benzyl-N-phenylamino group, N- (4-methoxybenzyl-N-phenylamino group, N-methyl-N- (o-tolyl) amino group, N-methyl-N- (m- Tolyl) amino group, N-methyl-N- (p-tolyl) amino group, N-ethyl-N- (m-tolyl) amino group, N-propyl-N- (m-tolyl) amino group, N-isopropyl -N- (m-tolyl) amino group, N-isopropyl-N- (p-tolyl) amino group, N-butyl-N- (m-tolyl) amino group, N-isobutyl-N- (m-tolyl) Amino group, N- (2-butyl) -N- (m-tolyl) amino group, N- (tert-butyl) -N- (m-tolyl) amino group, N-pentyl-N- (p-tolyl) Amino group, N-cyclopentyl-N- (m-tolyl) amino group N-hexyl-N- (m-tolyl) amino group, N-cyclohexyl-N- (p-tolyl) amino group, N-cyclohexylmethyl-N- (o-tolyl) amino group, N-heptyl-N- ( m-tolyl) amino group, N-octyl-N- (m-tolyl) amino group, N-nonyl-N- (m-tolyl) amino group, N-decyl-N- (p-tolyl) amino group, N -Dodecyl-N- (m-tolyl) amino group, N-benzyl-N- (m-tolyl) amino group, N- (4-fluorobenzyl) -N- (m-tolyl) amino group, N-methyl- N- (1-naphthyl) amino group, N-ethyl-N- (1-naphthyl) amino group, N- (1-naphthyl) -N-propylamino group, N-isopropyl-N- (1-naphthyl) amino Group, N-butyl-N- (1-naphthyl) amino group N- (2-butyl) -N- (1-naphthyl) amino group, N-isobutyl-N- (1-naphthyl) amino group, N- (tert-butyl) -N- (1-naphthyl) amino group N- (1-naphthyl) -N-pentylamino group, N-hexyl-N- (1-naphthyl) amino group, N-cyclohexyl-N- (1-naphthyl) amino group, N-cyclopentylmethyl-N- (1-naphthyl) amino group, N-heptyl-N- (1-naphthyl) amino group, N- (1-naphthyl) -N-octylamino group, N- (1-naphthyl) -N-nonylamino group, N -Decyl-N- (1-naphthyl) amino group, N-dodecyl-N- (1-naphthyl) amino group, N-benzyl-N- (1-naphthyl) amino group, N- (4-methoxybenzyl)- N- (1-naphthyl) amino group N- (1-naphthyl) -N- (2-phenethyl) amino group, N-methyl-N- (2-naphthyl) amino group, N-ethyl-N- (2-naphthyl) amino group, N- (2 -Naphthyl) -N-propylamino group, N-isopropyl-N- (2-naphthyl) amino group, N-butyl-N- (2-naphthyl) amino group, N-isobutyl-N- (2-naphthyl) amino Group, N- (2-butyl) -N- (2-naphthyl) amino group, N- (tert-butyl) -N- (2-naphthyl) amino group, N- (2-naphthyl) -N-pentylamino Group, N- (2-naphthyl) -N-isopentylamino group, N- (2-naphthyl) -N-neopentylamino group, N-cyclopentyl-N- (2-naphthyl) amino group, N-hexyl- N- (2-naphthyl) amino group, N-thio Rohexyl-N- (2-naphthyl) amino group, N-cyclohexylmethyl-N- (2-naphthyl) amino group, N-heptyl-N- (2-naphthyl) amino group, N- (2-naphthyl) -N -Octylamino group, N- (2-naphthyl) -N-nonylamino group, N-decyl-N- (2-naphthyl) amino group, N-dodecyl-N- (2-naphthyl) amino group, N-benzyl- N- (2-naphthyl) amino group, N- (4-fluorobenzyl) -N- (2-naphthyl) amino group, N- (4-methoxybenzyl) -N- (2-naphthyl) amino group, N- (2-naphthyl) -N- (2-phenethyl) amino group, N- (2-furfuryl) -N- (2-naphthyl) amino group, N- (1-anthryl) -N-methylamino group, N- (1-anthryl) -N-ethyla Mino group, N- (1-anthryl) -N-propylamino group, N- (1-anthryl) -N-isopropylamino group, N- (1-anthryl) -N-butylamino group, N- (1- Anthryl) -N- (2-butyl) amino group, N- (1-anthryl) -N- (tert-butyl) amino group, N- (1-anthryl) -N-isobutylamino group, N- (1- Anthryl) -N-pentylamino group, N- (1-anthryl) -N-isopentylamino group, N- (1-anthryl) -N-neopentylamino group, N- (1-anthryl) -N-cyclopentyl Amino group, N- (1-anthryl) -N-hexylamino group, N- (1-anthryl) -N-isohexylamino group, N- (1-anthryl) -N-cyclohexylamino group, N- (1 -Anne Ryl) -N-cyclohexylmethylamino group, N- (1-anthryl) -N-heptylamino group, N- (1-anthryl) -N-octylamino group, N- (1-anthryl) -N-nonylamino group N- (1-anthryl) -N-decylamino group, N- (1-anthryl) -N-dodecylamino group, N- (1-anthryl) -N-benzylamino group, N- (1-anthryl)- N- (4-fluorobenzyl) amino group, N- (1-anthryl) -N- (2-phenethyl) amino group, N-methyl-N- (9-phenanthryl) amino group, N-ethyl-N- ( 9-phenanthryl) amino group, N- (9-phenanthryl) -N-propylamino group, N-isopropyl-N- (9-phenanthryl) amino group, N-butyl-N- (9-phenanthate) ) Amino group, N-isobutyl-N- (9-phenanthryl) amino group, N- (2-butyl) -N- (2-phenanthryl) amino group, N- (tert-butyl) -N- (2- Phenanthryl) amino group, N-pentyl-N- (9-phenanthryl) amino group, N-isopentyl-N- (9-phenanthryl) amino group, N-neopentyl-N- (2-phenanthryl) amino group, N-cyclopentyl -N- (2-phenanthryl) amino group, N-hexyl-N- (9-phenanthryl) amino group, N-isohexyl-N- (9-phenanthryl) amino group, N-cyclohexyl-N- (2-phenanthryl) Amino group, N-cyclohexylmethyl-N- (9-phenanthryl) amino group, N-heptyl-N- (9-phenanthryl) amino Group, N-octyl-N- (9-phenanthryl) amino group, N-nonyl-N- (9-phenanthryl) amino group, N-decyl-N- (9-phenanthryl) amino group, N-dodecyl-N- (9-phenanthryl) amino group, N-benzyl-N- (9-phenanthryl) amino group, N- (4-dimethylaminobenzyl) -N- (9-phenanthryl) amino group, N-furfuryl-N- (9 -Phenanthryl) amino group, N- (9-phenanthryl) -N- (2-phenethyl) amino group, N- (9,9-dimethylfluoren-2-yl) -N-methylamino group, N- (9, 9-dimethylfluoren-2-yl) -N-ethylamino group, N- (9,9-dibutylfluoren-2-yl) -N-propylamino group, N- (9,9-dimethylfluorene) 2-yl) -N-isopropylamino group, N-butyl-N- (9,9-dihexylfluoren-2-yl) amino group, N- (9,9-dimethylfluoren-2-yl) -N-isobutyl Amino group, N- (2-butyl) -N- (9,9-diethylfluoren-2-yl) amino group, N- (tert-butyl) -N- (9,9-dimethylfluoren-2-yl) Amino group, N- (9,9-dibutylfluoren-2-yl) -N-pentylamino group, N- (9,9-dimethylfluoren-2-yl) -N-isopentylamino group, N-cyclopentyl- N- (9,9-dioctylfluoren-2-yl) amino group, N- (9,9-dimethylfluoren-2-yl) -N-hexylamino group, N- (9,9-diphenylfluorene-2- Il) -N Isohexylamino group, N-cyclohexyl-N- (9,9-diethylfluoren-2-yl) amino group, N-cyclohexylmethyl-N- (9,9-dimethylfluoren-2-yl) amino group, N- (9,9-dihexylfluoren-2-yl) -N-heptylamino group, N- (9,9-dimethylfluoren-2-yl) -N-octylamino group, N- (9,9-dibutylfluorene- 2-yl) -N-nonylamino group, N- (9,9-diphenylfluoren-2-yl) -N-decylamino group, N- (9,9-dimethylfluoren-2-yl) -N-dodecylamino group N-benzyl-N- (9,9-dimethylfluoren-2-yl) amino group, N- (9,9-dibutylfluoren-2-yl) -N- (4-methoxybenzyl) amino group N- (9,9-dimethylfluoren-2-yl) -N- (3-bromobenzyl) amino group, N- (9,9-dihexylfluoren-2-yl) -N-furfurylamino group, N -(9,9-dimethylfluoren-2-yl) -N- (2-phenylethyl) amino group, N- (9-fluoranthenyl) -N-methylamino group, N-ethyl-N- (9- Fluoranthenyl) amino group, N- (9-fluoranthenyl) -N-propylamino group, N- (9-fluoranthenyl) -N-isopropylamino group, N-butyl-N- (9-fluorane) Tenenyl) amino group, N- (9-fluoranthenyl) -N-isobutylamino group, N- (2-butyl) -N- (9-fluoranthenyl) amino group, N- (tert-butyl) -N -(9-Fluoranthenyl) amino Group, N- (9-fluoranthenyl) -N-pentylamino group, N- (9-fluoranthenyl) -N-isopentylamino group, N- (9-fluoranthenyl) -N-neopentylamino Group, N-cyclopentyl-N- (9-fluoranthenyl) amino group, N- (9-fluoranthenyl) -N-hexylamino group, N- (9-fluoranthenyl) -N-isohexylamino group N-cyclohexyl-N- (9-fluoranthenyl) amino group, N-cyclohexylmethyl-N- (9-fluoranthenyl) amino group, N- (9-fluoranthenyl) -N-heptylamino group, N- (9-fluoranthenyl) -N-octylamino group, N-decyl-N- (9-fluoranthenyl) amino group, N-dodecyl-N- (9-fluoranthenyl) amino group, N Benzyl-N- (9-fluoranthenyl) amino group, N- (9-fluoranthenyl) -N- (4-fluorobenzyl) amino group, N- (9-fluoranthenyl) -N- (4- Dimethylaminobenzyl) amino group, N- (9-fluoranthenyl) -N- (2-phenethyl) amino group, N- (3-fluoranthenyl) -N-methylamino group, N-ethyl-N- ( 3-fluoranthenyl) amino group, N- (3-fluoranthenyl) -N-propylamino group, N- (3-fluoranthenyl) -N-isopropylamino group, N-butyl-N- (3- Fluoranthenyl) amino group, N- (3-fluoranthenyl) -N-isobutylamino group, N- (2-butyl) -N- (3-fluoranthenyl) amino group, N- (tert-butyl) -N- (3-Fluora Nthenyl) amino group, N- (9-fluoranthenyl) -N-pentylamino group, N- (9-fluoranthenyl) -N-isopentylamino group, N- (3-fluoranthenyl) -N- Neopentylamino group, N-cyclopentyl-N- (3-fluoranthenyl) amino group, N- (3-fluoranthenyl) -N-hexylamino group, N- (3-fluoranthenyl) -N-iso Hexylamino group, N-cyclohexyl-N- (3-fluoranthenyl) amino group, N-cyclohexylmethyl-N- (3-fluoranthenyl) amino group, N- (3-fluoranthenyl) -N-heptyl Amino group, N- (3-fluoranthenyl) -N-octylamino group, N-decyl-N- (3-fluoranthenyl) amino group, N-dodecyl-N- (3-fluoranthenyl) Amino group, N-benzyl-N- (3-fluoranthenyl) amino group, N- (3-fluoranthenyl) -N- (3-fluorobenzyl) amino group, N- (3-fluoranthenyl)- N- (3-dimethylaminobenzyl) amino group, N- (3-fluoranthenyl) -N- (2-phenethyl) amino group, N-methyl-N- (1-pyrenyl) amino group, N-ethyl- N- (1-pyrenyl) amino group, N-propyl-N- (1-pyrenyl) amino group, N-isopropyl-N- (1-pyrenyl) amino group, N-butyl-N- (1-pyrenyl) amino group Group, N-isobutyl-N- (1-pyrenyl) amino group, N- (2-butyl) -N- (1-pyrenyl) amino group, N- (tert-butyl) -N- (1-pyrenyl) amino Group N-pentyl-N- (1-pyre ) Amino group, N-isopentyl-N- (1-pyrenyl) amino group, N-neopentyl-N- (1-pyrenyl) amino group, N-hexyl-N- (1-pyrenyl) amino group, N-isohexyl -N- (1-pyrenyl) amino group, N-cyclohexyl-N- (1-pyrenyl) amino group, N-cyclohexylmethyl-N- (1-pyrenyl) amino group, N-heptyl-N- (1-pyrenyl) ) Amino group, N-octyl-N- (1-pyrenyl) amino group, N-nonyl-N- (1-pyrenyl) amino group, N-decyl-N- (1-pyrenyl) amino group, N-dodecyl- N- (1-pyrenyl) amino group, N-benzyl-N- (1-pyrenyl) amino group, N- (4-fluorobenzyl) -N- (1-pyrenyl) amino group, N- (4-methoxybenzyl) ) -N- (1 -Pyrenyl) amino group, N- (2-phenethyl) -N- (1-pyrenyl) amino group, N-methyl-N- (3-perylenyl) amino group, N-ethyl-N- (3-perylenyl) amino Group, N-propyl-N- (3-perylenyl) amino group, N-isopropyl-N- (3-perylenyl) amino group, N-butyl-N- (3-perylenyl) amino group, N-isobutyl-N- (3-perylenyl) amino group, N- (2-butyl) -N- (3-perylenyl) amino group, N- (tert-butyl) -N- (3-perylenyl) amino group, N-pentyl-N- (3-perylenyl) amino group, N-isopentyl-N- (3-perylenyl) amino group, N-neopentyl-N- (3-perylenyl) amino group, N-cyclopentyl-N- (3-perylenyl) amino group, N-F Sil-N- (3-perylenyl) amino group, N-isohexyl-N- (3-perylenyl) amino group, N-cyclohexyl-N- (3-perylenyl) amino group, N-cyclohexylmethyl-N- (3- Perylenyl) amino group, N-heptyl-N- (3-perylenyl) amino group, N-octyl-N- (3-perylenyl) amino group, N-nonyl-N- (3-perylenyl) amino group, N-decyl -N- (3-perylenyl) amino group, N-undecyl-N- (3-perylenyl) amino group, N-dodecyl-N- (3-perylenyl) amino group, N-benzyl-N- (3-perylenyl) Examples thereof include an amino group, N- (4-methoxybenzyl) -N- (3-perylenyl) amino group, and N-furfuryl-N- (3-perylenyl) amino group.

Examples of the substituted or unsubstituted alkylheteroarylamino group having 5 to 40 carbon atoms include N-methyl-N- (2-pyridyl) amino group, N-methyl-N- (4-pyridyl) amino group, and N-ethyl. -N- (2-pyridyl) amino group, N-propyl-N- (2-pyridyl) amino group, N-isopropyl-N- (2-pyridyl) amino group, N-isopropyl-N- (4-pyridyl) Amino group, N-butyl-N- (2-pyridyl) amino group, N-butyl-N- (4-pyridyl) amino group, N-isobutyl-N- (2-pyridyl) amino group, N- (2- Butyl) -N- (2-pyridyl) amino group, N- (tert-butyl) -N- (2-pyridyl) amino group, N-pentyl-N- (2-pyridyl) amino group, N-isopentyl-N -(2-Pyridyl) amino N-neopentyl-N- (2-pyridyl) amino group, N-cyclopentyl-N- (2-pyridyl) amino group, N-hexyl-N- (2-pyridyl) amino group, N-hexyl-N- ( 4-pyridyl) amino group, N-isohexyl-N- (2-pyridyl) amino group, N-cyclohexyl-N- (2-pyridyl) amino group, N-cyclohexyl-N- (4-pyridyl) amino group, N -Cyclohexylmethyl-N- (2-pyridyl) amino group, N-heptyl-N- (2-pyridyl) amino group, N-octyl-N- (2-pyridyl) amino group, N-nonyl-N- (2 -Pyridyl) amino group, N-decyl-N- (2-pyridyl) amino group, N-dodecyl-N- (2-pyridyl) amino group, N-benzyl-N- (2-pyridyl) amino group, N- Benzyl N- (4-pyridyl) amino group, N- (4-fluorobenzyl) -N- (2-pyridyl) amino group, N- (2-phenethyl) -N- (2-pyridyl) amino group, N- ( 2-furyl) -N-methylamino group, N-ethyl-N- (2-furyl) amino group, N- (2-furyl) -N-propylamino group, N- (2-furyl) -N-isopropyl Amino group, N-butyl-N- (2-furyl) amino group, N- (2-furyl) -N-isobutylamino group, N- (2-butyl) -N- (2-furyl) amino group, N -(Tert-butyl) -N- (2-furyl) amino group, N- (2-furyl) -N-pentylamino group, N- (2-furyl) -N-isopentylamino group, N- (2 -Furyl) -N-neopentylamino group, N-cyclopentyl-N- (2-free ) Amino group, N- (2-furyl) -N-hexylamino group, N- (2-furyl) -N-isohexylamino group, N-cyclohexyl-N- (2-furyl) amino group, N- Cyclohexylmethyl-N- (2-furyl) amino group, N- (2-furyl) -N-heptylamino group, N- (2-furyl) -N-octylamino group, N- (2-furyl) -N -Nonylamino group, N-decyl-N- (2-furyl) amino group, N-dodecyl-N- (2-furyl) amino group, N-benzyl-N- (2-furyl) amino group, N- (4 -Fluorobenzyl) -N- (2-furyl) amino group, N- (2-furyl) -N- (2-phenethyl) amino group, N-methyl-N- (2-thienyl) amino group, N-ethyl -N- (2-thienyl) amino group, N-propyl-N- ( -Thienyl) amino group, N-isopropyl-N- (2-thienyl) amino group, N-butyl-N- (2-thienyl) amino group, N-isobutyl-N- (2-thienyl) amino group, N- (2-butyl) -N- (2-thienyl) amino group, N- (tert-butyl) -N- (2-thienyl) amino group, N-pentyl-N- (2-thienyl) amino group, N- Isopentyl-N- (2-thienyl) amino group, N-cyclopentyl-N- (2-thienyl) amino group, N-hexyl-N- (2-thienyl) amino group, N-isohexyl-N- (2-thienyl) ) Amino group, N-cyclohexyl-N- (2-thienyl) amino group, N-cyclohexylmethyl-N- (2-thienyl) amino group, N-heptyl-N- (2-thienyl) amino group, N-octyl -N (2-thienyl) amino group, N-nonyl-N- (2-thienyl) amino group, N-decyl-N- (2-thienyl) amino group, N-dodecyl-N- (2-thienyl) amino group, N-benzyl-N- (2-thienyl) amino group, N- (4-dimethylaminobenzyl) -N- (2-thienyl) amino group, N- (4-methoxybenzyl) -N- (2-thienyl) Amino group, N- (2-phenethyl) -N- (2-thienyl) amino group, N-furfuryl-N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N -Methylamino group, N- (benzo [b] furan-2-yl) -N-ethylamino group, N- (benzo [b] furan-2-yl) -N-propylamino group, N- (benzo [ b] furan-2-yl) -N-isopropylamino group, N -(Benzo [b] furan-2-yl) -N-butylamino group, N- (benzo [b] furan-2-yl) -N-isobutylamino group, N- (benzo [b] furan-2-yl Yl) -N- (2-butyl) amino group, N- (benzo [b] furan-2-yl) -N- (tert-butyl) amino group, N- (benzo [b] furan-2-yl) -N-pentylamino group, N- (benzo [b] furan-2-yl) -N-isopentylamino group, N- (benzo [b] furan-2-yl) -N-cyclopentylamino group, N- (Benzo [b] furan-2-yl) -N-hexylamino group, N- (benzo [b] furan-2-yl) -N-isohexylamino group, N- (benzo [b] furan-2-yl Yl) -N-cyclohexylamino group, N- (benzo [b] furan-2- ) -N-cyclohexylmethylamino group, N- (benzo [b] furan-2-yl) -N-heptylamino group, N- (benzo [b] furan-2-yl) -N-octylamino group, N- (benzo [b] furan-2-yl) -N-nonylamino group, N- (benzo [b] furan-2-yl) -N-decylamino group, N- (benzo [b] furan-2-yl ) -N-dodecylamino group, N- (benzo [b] furan-2-yl) -N-benzylamino group, N- (benzo [b] furan-2-yl) -N- (4-phenylbenzyl) Amino group, N- (benzo [b] furan-2-yl) -N- (2-phenethyl) amino group, N- (benzo [b] furan-2-yl) -N-furfurylamino group, N- (Benzo [b] thiophen-2-yl) -N-methylamino group N- (benzo [b] thiophen-2-yl) -N-ethylamino group, N- (benzo [b] thiophen-2-yl) -N-propylamino group, N- (benzo [b] thiophene-2 -Yl) -N-isopropylamino group, N- (benzo [b] thiophen-2-yl) -N-butylamino group, N- (benzo [b] thiophen-2-yl) -N-isobutylamino group, N- (benzo [b] thiophen-2-yl) -N- (2-butyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (tert-butyl) amino group, N- (Benzo [b] thiophen-2-yl) -N-pentylamino group, N- (benzo [b] thiophen-2-yl) -N-isopentylamino group, N- (benzo [b] thiophen-2-yl Yl) -N-neopentylamino group N- (benzo [b] thiophen-2-yl) -N-cyclopentylamino group, N- (benzo [b] thiophen-2-yl) -N-hexylamino group, N- (benzo [b] thiophene- 2-yl) -N-isohexylamino group, N- (benzo [b] thiophen-2-yl) -N-cyclohexylamino group, N- (benzo [b] thiophen-2-yl) -N-cyclohexylmethyl Amino group, N- (benzo [b] thiophen-2-yl) -N-heptylamino group, N- (benzo [b] thiophen-2-yl) -N-octylamino group, N- (benzo [b] Thiophen-2-yl) -N-nonylamino group, N- (benzo [b] thiophen-2-yl) -N-decylamino group, N- (benzo [b] thiophen-2-yl) -N-dodecylamino group , -(Benzo [b] thiophen-2-yl) -N-benzylamino group, N- (benzo [b] thiophen-2-yl) -N- (4-dimethylaminobenzyl) amino group, N- (benzo [ b] Thiophen-2-yl) -N-furfurylamino group, N-methyl-N- (1-methylindol-2-yl) amino group, N-ethyl-N- (1-methylindol-2-yl) ) Amino group, N- (1-methylindol-2-yl) -N-propylamino group, N-isopropyl-N- (1-methylindol-2-yl) amino group, N-butyl-N- (1 -Methylindol-2-yl) amino group, N-isobutyl-N- (1-methylindol-2-yl) amino group, N- (2-butyl) -N- (1-methylindol-2-yl) Amino group, N- (te t-butyl) -N- (1-methylindol-2-yl) amino group, N- (1-methylindol-2-yl) -N-pentylamino group, N-isopentyl-N- (1-methylindole) -2-yl) amino group, N-cyclopentyl-N- (1-methylindol-2-yl) amino group, N-neopentyl-N- (1-methylindol-2-yl) amino group, N-hexyl- N- (1-methylindol-2-yl) amino group, N-isohexyl-N- (1-methylindol-2-yl) amino group, N-cyclohexyl-N- (1-methylindol-2-yl) Amino group, N-cyclohexylmethyl-N- (1-methylindol-2-yl) amino group, N-heptyl-N- (1-methylindol-2-yl) amino group, N- (1- Methylindol-2-yl) -N-octylamino group, N- (1-methylindol-2-yl) -N-nonylamino group, N-decyl-N- (1-methylindol-2-yl) amino group N-dodecyl-N- (1-methylindol-2-yl) amino group, N-benzyl-N- (1-methylindol-2-yl) amino group, N- (4-fluorobenzyl) -N- (1-methylindol-2-yl) amino group, N- (1-methylindol-2-yl) -N- (2-phenethyl) amino group, N- (dibenzofuran-2-yl) -N-methylamino Group, N- (dibenzofuran-3-yl) -N-methylamino group, N- (dibenzofuran-3-yl) -N-ethylamino group, N- (dibenzofuran-3-yl) -N-propylamino group, N (Dibenzofuran-2-yl) -N-isopropylamino group, N- (dibenzofuran-3-yl) -N-isopropylamino group, N-butyl-N- (dibenzofuran-3-yl) amino group, N- (2 -Butyl) -N- (dibenzofuran-3-yl) amino group, N- (tert-butyl) -N- (dibenzofuran-3-yl) amino group, N- (dibenzofuran-3-yl) -N-pentylamino Group, N- (dibenzofuran-3-yl) -N-isopentylamino group, N- (dibenzofuran-3-yl) -N-neopentylamino group, N-cyclopentyl-N- (dibenzofuran-3-yl) amino Group, N- (dibenzofuran-2-yl) -N-hexylamino group, N- (dibenzofuran-3-yl) -N-hexylamino group, N- (dibenzo Lan-3-yl) -N-isohexylamino group, N-cyclohexyl-N- (dibenzofuran-3-yl) amino group, N-cyclohexylmethyl-N- (dibenzofuran-3-yl) amino group, N- ( Dibenzofuran-3-yl) -N-heptylamino group, N- (dibenzofuran-2-yl) -N-octylamino group, N- (dibenzofuran-3-yl) -N-octylamino group, N- (dibenzofuran- 3-yl) -N-nonylamino group, N-decyl-N- (dibenzofuran-3-yl) amino group, N- (dibenzofuran-3-yl) -N-dodecylamino group, N-benzyl-N- (dibenzofuran) -2-yl) amino group, N-benzyl-N- (dibenzofuran-3-yl) amino group, N- (dibenzofuran-3-yl) -N- (dimethyl) Aminobenzyl) amino group, N- (dibenzofuran-3-yl) -N- (2-phenethyl) amino group, N- (dibenzofuran-3-yl) -N-furfurylamino group, N- (dibenzothiophene-2) -Yl) -N-methylamino group, N- (dibenzothiophen-3-i
) -N-methylamino group, N- (dibenzothiophen-3-yl) -N-ethylamino group, N- (dibenzothiophen-3-yl) -N-propylamino group, N- (dibenzothiophene-2) -Yl) -N-isopropylamino group, N- (dibenzothiophen-3-yl) -N-isopropylamino group, N-butyl-N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophene- 2-yl) -N-isobutylamino group, N- (dibenzothiophen-3-yl) -N-isobutylamino group, N- (2-butyl) -N- (dibenzothiophen-3-yl) amino group, N -(Tert-butyl) -N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N-pentylamino group, N- (dibenzo Offen-3-yl) -N-isopentylamino group, N- (dibenzothiophen-3-yl) -N-neopentylamino group, N-cyclopentyl-N- (dibenzothiophen-3-yl) amino group, N -(Dibenzothiophen-2-yl) -N-hexylamino group, N- (dibenzothiophen-3-yl) -N-hexylamino group, N- (dibenzothiophen-3-yl) -N-isohexylamino group N-cyclohexyl-N- (dibenzothiophen-3-yl) amino group, N-cyclohexylmethyl-N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N-heptyl Amino group, N- (dibenzothiophen-2-yl) -N-octylamino group, N- (dibenzothiophen-3-yl) -N-o Tilamino group, N- (dibenzothiophen-3-yl) -N-nonylamino group, N-decyl-N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N-dodecyl Amino group, N-benzyl-N- (dibenzothiophen-2-yl) amino group, N-benzyl-N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N- (4-Fluorobenzyl) amino group, N- (dibenzothiophen-3-yl) -N- (4-methoxybenzyl) amino group, N- (dibenzothiophen-2-yl) -N- (2-phenethyl) amino Group, N- (dibenzothiophen-3-yl) -N- (2-phenethyl) amino group, N- (dibenzothiophen-3-yl) -N-furfurylamino group, N -Methyl-N- (2-quinolyl) amino group, N-methyl-N- (3-quinolyl) amino group, N-methyl-N- (4-quinolyl) amino group, N-methyl-N- (5- Quinolyl) amino group, N-methyl-N- (8-quinolyl) amino group, N-ethyl-N- (2-quinolyl) amino group, N-propyl-N- (2-quinolyl) amino group, N-isopropyl -N- (2-quinolyl) amino group, N-butyl-N- (2-quinolyl) amino group, N-isobutyl-N- (2-quinolyl) amino group, N- (2-butyl) -N- ( 2-quinolyl) amino group, N- (tert-butyl) -N- (2-quinolyl) amino group, N-pentyl-N- (2-quinolyl) amino group, N-isopentyl-N- (2-quinolyl) Amino group, N-neopentyl-N- (2-quinolyl) Mino group, N-cyclopentyl-N- (2-quinolyl) amino group, N-hexyl-N- (2-quinolyl) amino group, N-hexyl-N- (3-quinolyl) amino group, N-hexyl-N -(4-quinolyl) amino group, N-isohexyl-N- (2-quinolyl) amino group, N-cyclohexyl-N- (2-quinolyl) amino group, N-cyclohexylmethyl-N- (2-quinolyl) amino Group, N-heptyl-N- (2-quinolyl) amino group, N-octyl-N- (2-quinolyl) amino group, N-octyl-N- (4-quinolyl) amino group, N-octyl-N- (8-quinolyl) amino group, N-nonyl-N- (2-quinolyl) amino group, N-decyl-N- (2-quinolyl) amino group, N-dodecyl-N- (2-quinolyl) amino group, N-benzyl-N (2-quinolyl) amino group, N-benzyl-N- (4-quinolyl) amino group, N-benzyl-N- (5-quinolyl) amino group, N-benzyl-N- (8-quinolyl) amino group, N- (4-methoxybenzyl) -N- (2-quinolyl) amino group, N- (2-phenethyl) -N- (2-quinolyl) amino group, N- (1-isoquinolyl) -N-methylamino group N- (3-isoquinolyl) -N-methylamino group, N- (4-isoquinolyl) -N-methylamino group, N- (6-isoquinolyl) -N-methylamino group, N-ethyl-N- ( 1-isoquinolyl) amino group, N- (1-isoquinolyl) -N-propylamino group, N-isopropyl-N- (1-isoquinolyl) amino group, N-butyl-N- (1-isoquinolyl) amino group, N -Isobutyl-N -(1-isoquinolyl) amino group, N- (2-butyl) -N- (1-isoquinolyl) amino group, N- (tert-butyl) -N- (1-isoquinolyl) amino group, N- (1- Isoquinolyl) -N-pentylamino group, N-isopentyl-N- (1-isoquinolyl) amino group, N- (1-isoquinolyl) -N-neopentylamino group, N-cyclopentyl-N- (1-isoquinolyl) amino Group, N-hexyl-N- (1-isoquinolyl) amino group, N-isohexyl-N- (1-isoquinolyl) amino group, N-cyclohexyl-N- (1-isoquinolyl) amino group, N-cyclohexylmethyl-N -(1-isoquinolyl) amino group, N-heptyl-N- (1-isoquinolyl) amino group, N- (1-isoquinolyl) -N-octylamino group, N- 1-isoquinolyl) -N-nonylamino group, N-decyl-N- (1-isoquinolyl) amino group, N-dodecyl-N- (1-isoquinolyl) amino group, N-benzyl-N- (1-isoquinolyl) amino Group, N- (4-fluorobenzyl) -N- (1-isoquinolyl) amino group, N- (1-isoquinolyl) -N- (4-methoxybenzyl) amino group, N- (1-isoquinolyl) -N- (2-phenethyl) amino group, N-methyl-N- (2-quinazolinyl) amino group, N-methyl-N- (4-quinazolinyl) amino group, N-methyl-N- (5-quinazolinyl) amino group, N-methyl-N- (6-quinazolinyl) amino group, N-ethyl-N- (2-quinazolinyl) amino group, N-propyl-N- (2-quinazolinyl) amino group, N-isopropyl- -(2-quinazolinyl) amino group, N-butyl-N- (2-quinazolinyl) amino group, N-isobutyl-N- (2-quinazolinyl) amino group, N- (2-butyl) -N- (2- Quinazolinyl) amino group, N- (tert-butyl) -N- (2-quinazolinyl) amino group, N-pentyl-N- (2-quinazolinyl) amino group, N-isopentyl-N- (2-quinazolinyl) amino group N-cyclopentyl-N- (2-quinazolinyl) amino group, N-hexyl-N- (2-quinazolinyl) amino group, N-isohexyl-N- (2-quinazolinyl) amino group, N-cyclohexyl-N- ( 2-quinazolinyl) amino group, N-cyclohexylmethyl-N- (2-quinazolinyl) amino group, N-heptyl-N- (2-quinazolinyl) amino group, N-octyl Tyl-N- (2-quinazolinyl) amino group, N-nonyl-N- (2-quinazolinyl) amino group, N-decyl-N- (2-quinazolinyl) amino group, N- (2-quinazolinyl) -N- Undecylamino group, N-dodecyl-N- (2-quinazolinyl) amino group, N-benzyl-N- (2-quinazolinyl) amino group, N- (4-dimethylaminobenzyl) -N- (2-quinazolinyl) Amino group, N- (4-methoxybenzyl) -N- (2-quinazolinyl) amino group, N- (2-phenethyl) -N- (2-quinazolinyl) amino group, N-methyl-N- (2-quinoxalinyl) ) Amino group, N-methyl-N- (5-quinoxalinyl) amino group, N-methyl-N- (6-quinoxalinyl) amino group, N-ethyl-N- (2-quinoxalinyl) amino group, N- Lopyl-N- (2-quinoxalinyl) amino group, N-isopropyl-N- (2-quinoxalinyl) amino group, N-butyl-N- (2-quinoxalinyl) amino group, N-isobutyl-N- (2-quinoxalinyl) ) Amino group, N- (2-butyl) -N- (2-quinoxalinyl) amino group, N- (tert-butyl) -N- (2-quinoxalinyl) amino group, N-pentyl-N- (2-quinoxalinyl) ) Amino group, N-isopentyl-N- (2-quinoxalinyl) amino group, N-cyclopentyl-N- (2-quinoxalinyl) amino group, N-hexyl-N- (2-quinoxalinyl) amino group, N-cyclohexyl- N- (2-quinoxalinyl) amino group, N-cyclohexylmethyl-N- (2-quinoxalinyl) amino group, N-heptyl-N- ( -Quinoxalinyl) amino group, N-octyl-N- (2-quinoxalinyl) amino group, N-nonyl-N- (2-quinoxalinyl) amino group, N-decyl-N- (2-quinoxalinyl) amino group, N- Dodecyl-N- (2-quinoxalinyl) amino group, N-benzyl-N- (2-quinoxalinyl) amino group, N- (4-fluorobenzyl) -N- (2-quinoxalinyl) amino group, N- (3- Methoxybenzyl) -N- (2-quinoxalinyl) amino group, N- (2-phenethyl) -N- (2-quinoxalinyl) amino group, N-furfuryl-N- (2-quinoxalinyl) amino group, N-methyl- N- (9-methylcarbazol-2-yl) amino group, N-methyl-N- (9-phenylcarbazol-2-yl) amino group, N-methyl-N- (9- Methylcarbazol-3-yl) amino group, N-methyl-N- (9-phenylcarbazol-3-yl) amino group, N-ethyl-N- (9-methylcarbazol-2-yl) amino group, N- (9-methylcarbazol-2-yl) -N-propylamino group, N-isopropyl-N- (9-methylcarbazol-2-yl) amino group, N-butyl-N- (9-methylcarbazole-2- Yl) amino group, N-butyl-N- (9-methylcarbazol-3-yl) amino group, N-isobutyl-N- (9-methylcarbazol-2-yl) amino group, N- (2-butyl) -N- (9-methylcarbazol-2-yl) amino group, N- (tert-butyl) -N- (9-methylcarbazol-2-yl) amino group, N- (9-methylcarbazol-2) Yl) -N-pentylamino group, N-isopentyl-N- (9-methylcarbazol-2-yl) amino group, N-neopentyl-N- (9-methylcarbazol-2-yl) amino group, N-cyclopentyl -N- (9-methylcarbazol-2-yl) amino group, N-hexyl-N- (9-methylcarbazol-2-yl) amino group, N-hexyl-N- (9-phenylcarbazol-2-yl) ) Amino group, N-hexyl-N- (9-phenylcarbazol-3-yl) amino group, N-isohexyl-N- (9-methylcarbazol-2-yl) amino group, N-cyclohexyl-N- (9 -Methylcarbazol-2-yl) amino group, N-cyclohexylmethyl-N- (9-methylcarbazol-2-yl) amino group, N-heptyl-N- 9-methylcarbazol-2-yl) amino group, N- (9-methylcarbazol-2-yl) -N-nonylamino group, N- (9-methylcarbazol-2-yl) -N-octylamino group, N -Decyl-N- (9-methylcarbazol-2-yl) amino group, N-dodecyl-N- (9-methylcarbazol-2-yl) amino group, N-benzyl-N- (9-methylcarbazole-2) -Yl) amino group, N-benzyl-N- (9-methylcarbazol-3-yl) amino group, N-benzyl-N- (9-ethylcarbazol-2-yl) amino group, N- (4-dimethyl) Aminobenzyl) -N- (9-methylcarbazol-2-yl) amino, N- (4-fluorobenzyl) -N- (9-methylcarbazol-2-yl) amino, N- (9-me Tylcarbazol-2-yl) -N- (2-phenethyl) amino group, N-furfuryl-N- (9-methylcarbazol-2-yl) amino group, N- (1-acridinyl) -N-methylamino group N- (2-acridinyl) -N-methylamino group, N- (3-acridinyl
) -N-methylamino group, N- (4-acridinyl) -N-methylamino group, N- (9-acridinyl) -N-methylamino group, N- (9-acridinyl) -N-ethylamino group, N- (9-acridinyl) -N-propylamino group, N- (9-acridinyl) -N-isopropylamino group, N- (9-acridinyl) -N-butylamino group, N- (9-acridinyl)- N-isobutylamino group, N- (9-acridinyl) -N- (2-butyl) amino group, N- (9-acridinyl) -N- (tert-butyl) amino group, N- (9-acridinyl)- N-pentylamino group, N- (9-acridinyl) -N-isopentylamino group, N- (9-acridinyl) -N-neopentylamino group, N- (9-acridinyl) -N-cyclopentyl Amino group, N- (9-acridinyl) -N-hexylamino group, N- (9-acridinyl) -N-isopropylamino group, N- (9-acridinyl) -N-cyclohexylamino group, N- (9 -Acridinyl) -N-cyclohexylmethylamino group, N- (9-acridinyl) -N-heptylamino group, N- (9-acridinyl) -N-octylamino group, N- (9-acridinyl) -N-nonylamino Group, N- (9-acridinyl) -N-decylamino group, N- (9-acridinyl) -N-undecylamino group, N- (9-acridinyl) -N-dodecylamino group, N- (9-acridinyl) ) -N-benzylamino group, N- (9-acridinyl) -N- (4-dimethylaminobenzyl) amino group, N- (9-acridinyl) -N- (4- Toxibenzyl) amino group, N- (9-acridinyl) -N- (2-phenethyl) amino group, N- (9-acridinyl) -N-furfurylamino group, N-methyl-N- (1,10- Phenanthrolin-2-yl) amino group, N-methyl-N- (1,10-phenanthroline-3-yl) amino group, N-methyl-N- (1,10-phenanthroline-4-yl) amino group, N -Methyl-N- (1,10-phenanthroline-5-yl) amino group, N-ethyl-N- (1,10-phenanthroline-2-yl) amino group, N- (1,10-phenanthroline-2- Yl) -N-propylamino group, N-isopropyl-N- (1,10-phenanthrolin-2-yl) amino group, N-butyl-N- (1,10-phenanthroline-2-yl) amino Group, N-butyl-N- (1,10-phenanthroline-3-yl) amino group, N-butyl-N- (1,10-phenanthroline-4-yl) amino group, N-butyl-N- (1 , 10-phenanthroline-5-yl) amino group, N-isobutyl-N- (1,10-phenanthroline-2-yl) amino group, N- (2-butyl) -N- (1,10-phenanthroline-2 -Yl) amino group, N- (tert-butyl-N- (1,10-phenanthroline-2-yl) amino group, N-pentyl-N- (1,10-phenanthroline-2-yl) amino group, N -Isopentyl-N- (1,10-phenanthrolin-2-yl) amino group, N-neopentyl-N- (1,10-phenanthrolin-2-yl) amino group, N-cyclopentyl-N- (1, 0-phenanthroline-2-yl) amino group, N-hexyl-N- (1,10-phenanthroline-2-yl) amino group, N-isohexyl-N- (1,10-phenanthroline-2-yl) amino group N-cyclohexyl-N- (1,10-phenanthroline-2-yl) amino group, N-cyclohexyl-N- (1,10-phenanthroline-3-yl) amino group, N-cyclohexyl-N- (1, 10-phenanthroline-4-yl) amino group, N-cyclohexylmethyl-N- (1,10-phenanthroline-2-yl) amino group, N-cyclohexylmethyl-N- (1,10-phenanthroline-5-yl) Amino group, N-heptyl-N- (1,10-phenanthrolin-2-yl) amino group, N-octyl-N- (1,10-phenyl) Nantrolin-2-yl) amino group, N-nonyl-N- (1,10-phenanthrolin-2-yl) amino group, N-decyl-N- (1,10-phenanthrolin-2-yl) amino group, N -Dodecyl-N- (1,10-phenanthrolin-2-yl) amino group, N-benzyl-N- (1,10-phenanthrolin-2-yl) amino group, N- (4-methoxybenzyl) -N- (1,10-phenanthroline-2-yl) amino group, N- (1,10-phenanthroline-2-yl) -N- (2-phenethyl) amino group, N-furfuryl-N- (1,10-phenanthroline -2-yl) amino group, N-methyl-N- (1-phenazinyl) amino group, N-methyl-N- (2-phenazinyl) amino group, N-ethyl-N- (2-phenazinyl) amino Group, N- (2-phenazinyl) -N-propylamino group, N-isopropyl-N- (2-phenazinyl) amino group, N-butyl-N- (2-phenazinyl) amino group, N-isobutyl-N -(2-phenazinyl) amino group, N- (2-butyl) -N- (2-phenazinyl) amino group, N- (tert-butyl) -N- (2-phenazinyl) amino group, N-pentyl-N -(2-phenazinyl) amino group, N-isopentyl-N- (2-phenazinyl) amino group, N-neopentyl-N- (2-phenazinyl) amino group, N-cyclopentyl-N- (2-phenazinyl) amino group N-hexyl-N- (2-phenazinyl) amino group, N-isohexyl-N- (2-phenazinyl) amino group, N-cyclohexyl-N- (2-phenazinyl) Mino group, N-cyclohexylmethyl-N- (2-phenazinyl) amino group, N-heptyl-N- (2-phenazinyl) amino group, N-octyl-N- (2-phenazinyl) amino group, N-nonyl- N- (2-phenazinyl) amino group, N-decyl-N- (2-phenazinyl) amino group, N-dodecyl-N- (2-phenazinyl) amino group, N-benzyl-N- (2-phenazinyl) amino Group, N- (4-dimethylaminobenzyl) -N- (2-phenazinyl) amino group, N- (4-fluorobenzyl) -N- (2-phenazinyl) amino group, N- (2-phenazinyl) -N -(2-phenethyl) amino group, N-furfuryl-N- (2-phenazinyl) amino group and the like can be mentioned.

Examples of the substituent in the case of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms include an alkoxy group, a dialkylamino group, and a cyano group.
Examples of the substituent in the case of a substituted or unsubstituted alkenyl group having 3 to 20 carbon atoms include an alkoxy group, an aryl group, and a perfluoroalkyl group.
Examples of the substituent in the case of a substituted or unsubstituted aryl group having 6 to 45 carbon atoms include a halogen atom, an alkyl group, an alkoxy group, a dialkylamino group, and a diarylamino group.
Examples of the substituent in the case of a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms include an aryl group, an alkoxy group, a dialkylamino group, and a diarylamino group.
Examples of the substituent in the case of a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms include a halogen atom, an aryl group, an alkoxy group, a dialkylamino group, and a cyano group.
Examples of the substituent in the case of a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms include a halogen atom, an alkyl group, an alkoxy group, and a dialkylamino group.
Examples of the substituent in the case of a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms include an alkoxy group.
Examples of the substituent in the case of a substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms include a halogen atom, an alkyl group, an alkoxy group, a dialkylamino group, and a diarylamino group.
Examples of the substituent in the case of a substituted or unsubstituted arylheteroarylamino group having 10 to 40 carbon atoms include a halogen atom, an alkyl group, an alkoxy group, an aryl group, a dialkylamino group, and a diarylamino group.
Examples of the substituent in the case of a substituted or unsubstituted alkylarylamino group having 7 to 40 carbon atoms include a halogen atom, an alkyl group, an alkoxy group, and a dialkylamino group.
Examples of the substituent in the case of a substituted or unsubstituted alkylheteroarylamino group having 5 to 40 carbon atoms include a halogen atom, an alkyl group, an alkoxy group, an aryl group, a dialkylamino group, and a diarylamino group.

  Preferred specific examples of the 1,10-phenanthroline compound represented by the general formula (1) are shown below, but are not limited thereto.

  The compound of the general formula (1) of the present invention can be efficiently produced by the production method of claim 2.

  The compound of the present invention is a reaction in which an amino compound represented by the general formula (2) and an α-methylenecarbonyl compound represented by the general formula (3) are condensed and cyclized in the presence of a base or an acid to form a pyridine ring. (Friedlander reaction) [Organic Reactions, 28, 37].

8-Aminoquinoline-7-carbaldehyde, which is one of the amino compounds represented by the general formula (2) used for the production of the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention, is known. It can be manufactured by a manufacturing method [J. Org. Chem. , 61 , 3017 (1996), Tetrahedron, 36 , 10685 (1994). ]. Alternatively, 8-aminoquinoline-7-carbaldehyde can be chemically converted to produce a 7-acyl-8-aminoquinoline derivative.

The α-methylenecarbonyl compound represented by the general formula (3) can be produced by a known production method [Can. J. et al. Chem. , 46 , 715 (1968)].

  The 1,10-phenanthroline derivative represented by the general formula (1) of the present invention is usually reacted in the presence of a base or an acid. Examples of the base used in the production of the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention include, for example, alkali hydroxides, tetraalkylammonium hydroxides, amines, alkali metal alkoxides. and so on. Examples of the alkali hydroxides include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide and the like. Examples of tetraalkylammonium hydroxides include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, and the like. Examples of amines include dimethylamine, diethylamine, piperidine, morpholine, pyridine and the like. Examples of alkali metal alkoxides include sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, potassium tert-butoxide, etc. Piperidine is preferred.

  Examples of the acid used in the production of the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention include hydrochloric acid, sulfuric acid, acetic acid, phosphoric acid, polyphosphoric acid, phosphorus pentoxide, ammonium acetate, and the like. In addition, metal salts having Lewis acidity such as zinc chloride and zinc bromide can be exemplified, but hydrochloric acid and sulfuric acid are particularly preferable.

  The production of the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention can be usually carried out in the atmosphere, but when the base used is an alkali metal alkoxide, dry nitrogen, argon, etc. In an inert atmosphere.

  Examples of the solvent used include water, methanol, ethanol, butanol, glycerin, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, dimethyl sulfoxide and the like when the reaction is performed in the presence of a base. Preferred are ethanol, tetrahydrofuran and dimethyl sulfoxide. More preferred are ethanol and dimethyl sulfoxide. A plurality of solvents may be mixed and used. When the base used is an alkali metal alkoxide, a dehydrated and dried solvent is used. Examples of the solvent used when the reaction is performed in the presence of an acid include acetic acid, chlorobenzene, toluene, ethanol and the like. Preferably, it is acetic acid. The amount of the solvent used is suitably 5 to 100 times the weight of the compound represented by the general formula (2). The reaction temperature ranges from room temperature to 200 ° C. The reaction time is about 0.5 to 72 hours.

When the reaction is carried out in the presence of a base, it is cooled after completion of the reaction, the precipitated crystals are filtered, washed with ethanol and water, and dried to obtain the desired product. If crystals do not precipitate even after cooling, the reaction solution is poured into ethanol, methanol or water, the precipitated crystals are filtered, washed with ethanol, methanol or water, and dried to obtain the desired product. It is done. If crystals do not precipitate even when the reaction solution is poured into ethanol, methanol or water, extraction with a solvent such as chloroform, dichloromethane or ethyl acetate, washing, drying and concentration yields the desired product.
When the reaction is carried out in the presence of an acid, the reaction is cooled after completion of the reaction, the reaction solution is poured into an alkaline aqueous solution to make it basic, the precipitated crystals are filtered, washed with methanol or water, and dried. A product is obtained. If crystals do not precipitate even after being poured into an alkaline aqueous solution and made basic, extraction with a solvent such as chloroform, dichloromethane, or ethyl acetate, washing, drying, and concentration yields the desired product.

  The product can be purified by recrystallization, column chromatography, or sublimation as necessary. Moreover, you may combine the said 3 purification methods as needed. Examples of the purification solvent include N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, toluene, ethyl acetate, chloroform and the like.

  When a substituent is introduced into the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention, the compound represented by the general formula (2) and the α-methylenecarbonyl compound represented by the general formula (3) are previously introduced. There is a method in which a desired substituent is introduced and two compounds are condensed and cyclized. In addition, a 1,10-phenanthroline derivative represented by the general formula (1) in which a halogen atom such as a chlorine atom, a bromine atom, or an iodine atom is substituted at the substitution position to be introduced is synthesized, and then the halogen atom is substituted as desired. There is also a method of replacing the group. Examples of the reaction for replacing the halogen atom with other substituents include, for example, the Suzuki coupling reaction [Chem. Rev. , Vol. 102, 1359 (2002)], when replacing with a substituted amino group, Ullmann reaction [Organic Synthesis, Vol. 1, page 544], or amination reaction using a palladium catalyst [Topics in Current Chem. , 219, 131].

  Next, combinations of specific compounds of the 1,10-phenanthroline derivative represented by the general formula (1) and raw materials for production thereof are shown in the following table.

Specific example of production of 1,10-phenanthroline derivative represented by the general formula (1)

  The 1,10-phenanthroline derivative represented by the general formula (1) of the present invention has high electron transport performance and excellent properties as a fluorescent material. Therefore, it can be used as an electron injection material, an electron transport material, and a light emitting material.

  When the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention is used in an organic electroluminescence device, it can be used as a host material or a dopant. Moreover, since the compound of this invention has high electron transport performance, it can be used as an electron transport material and an electron injection material.

  When the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention is used for an electron transport layer, it can be used as an electron injection material, an electron transport material, or a light emitting material. When used as an electron transport material, various fluorescent materials can be used as a dopant. The electron transport layer may be a layer containing a dopant.

  Each of the hole transport layer, the electron transport layer, and the light emitting layer may have a single layer structure or a multilayer structure. In addition, each of the hole transport layer and the electron transport layer is divided into a layer responsible for the injection function (hole injection layer and electron injection layer) and a layer responsible for the transport function (hole transport layer and electron transport layer). It can also be provided.

  Next, the organic electroluminescent element of the present invention will be described. The organic electroluminescent device of the present invention is a device in which one or more organic compound layers are laminated between an anode and a cathode, and at least one of the organic compound layers is represented by 1,10 represented by the general formula (1) of the present invention. -Contains a phenanthroline derivative. When the organic electroluminescent element is a single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole transport material or an electron transport material for the purpose of transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. A plurality of light emitting materials may be mixed. Examples of the configuration of the multilayer organic electroluminescent device include, for example, anode / hole transport layer / light emitting layer / cathode, anode / light emitting layer / electron transport layer / cathode, anode / hole transport layer / light emitting layer / electron transport. Layer / cathode, anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode, anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, anode / hole injection Examples of such layers include a multilayer structure such as layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode. Further, a sealing layer may be provided on the cathode as necessary.

  The organic electroluminescent element of the present invention is not limited to the above configuration example, and can have various configurations. If necessary, a layer in which a hole transport layer component and a light emitting layer component or an electron transport layer component and a light emitting layer component are mixed may be provided.

Hereinafter, the constituent elements of the organic electroluminescence device of the present invention will be described in detail by taking as an example the device configuration comprising an anode / hole transport layer / light emitting layer / electron transport layer / cathode. The organic electroluminescent device of the present invention is preferably supported on a substrate. There is no restriction | limiting in particular about the raw material of a board | substrate, What is necessary is just what is conventionally used for the conventional organic electroluminescent element, For example, what consists of glass, transparent plastic, quartz glass etc. can be used. As an anode of the organic electroluminescence device of the present invention, a metal having a large work function (4 eV or more) possessed by the metal, an alloy having a large work function (4 eV or greater) possessed by the alloy, or a conductive material and a mixture thereof are used as electrode materials. It is preferable that Specific examples of such an electrode material include, for example, metals such as gold, silver, and copper, conductive transparent materials such as ITO (indium tin oxide), tin oxide (SnO ₂ ), and zinc oxide (ZnO), Examples thereof include conductive polymer materials such as polypyrrole and polythiophene. For the anode, these electrode materials can be formed on the substrate by, for example, vapor deposition, sputtering, coating, or the like. The sheet electrical resistance of the anode is preferably several hundred Ω / cm ² or less. Although the film thickness of the anode depends on the material, it is generally about 5 to 1,000 nm, preferably 10 to 500 nm.

As the cathode, an electrode material is preferably a metal having a small work function (4 eV or less) possessed by the metal, an alloy having a small work function (4 eV or less) possessed by the alloy, a conductive substance, or a mixture thereof. Specific examples of such electrode materials include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, magnesium, magnesium-silver alloy, magnesium-indium alloy, aluminum, aluminum-lithium alloy, and aluminum-magnesium alloy. Can be mentioned. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet electrical resistance of the cathode is preferably several hundred Ω / cm ² or less. The thickness of the cathode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm. In order to efficiently extract light emitted from the organic electroluminescent element of the present invention, at least one of the anode and the cathode is preferably transparent or translucent.

The hole transport layer of the organic electroluminescence device of the present invention is made of a hole transfer compound and has a function of transferring holes injected from the anode to the light emitting layer. A hole transport compound having a hole mobility of at least 10 ⁻⁶ cm ² / V · sec when a hole transport compound is disposed between two electrodes to which an electric field is applied and holes are injected from an anode Is preferred. The hole transport compound used for the hole transport layer of the organic electroluminescence device of the present invention is not particularly limited as long as it has the above-mentioned preferable properties. It is possible to select and use any one of materials that have been conventionally used as a charge injecting and transporting material for holes in photoconductive materials and known materials that are used for the hole transporting layer of organic electroluminescent devices. it can.

  Examples of the hole transfer material include phthalocyanine derivatives such as copper phthalocyanine, N, N, N ′, N′-tetraphenyl-1,4-phenylenediamine, and N, N′-di (m-tolyl)-. N, N′-diphenyl-4,4′-diaminobiphenyl (TPD), N, N′-di (1-naphthyl) -N, N′-diphenyl-4,4′-diaminobiphenyl (α-NPD), etc. And triarylamine derivatives, polyphenylene vinylene derivatives, polythiophene derivatives, and water-soluble PEDOT (polyethylenedioxythiophene) -PSS (polystyrene sulfonic acid). The hole transport layer may be composed of one or more of these hole transport compounds, or may be a laminate of hole transport layers composed of a compound different from the above hole transport compound. .

  As the light emitting material of the light emitting layer of the organic electroluminescent device of the present invention, a 1,10-phenanthroline derivative represented by the general formula (1) of the present invention is preferable. When the light-emitting material is not the 1,10-phenanthroline derivative of the present invention, the light-emitting material of the light-emitting layer is not particularly limited, and any one of conventionally known compounds can be selected and used. it can.

  Examples of the light emitting material other than the 1,10-phenanthroline derivative represented by the general formula (1) include an acridone derivative, a quinacridone derivative, a coumarin derivative (for example, coumarin 1, coumarin 6, coumarin 110, coumarin 153), a pyran derivative (for example, DCM1, DCM2), oxazone derivatives (eg Nile red), benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, condensed polycyclic aromatic hydrocarbons and their derivatives (eg pyrene, perylene, rubrene, chrysene), tria Examples thereof include a reelamine derivative and an organometallic complex [for example, tris (8-hydroxyquinolinato) aluminum (Alq3), tris (2-phenylpyridine) iridium].

  When a 1,10-phenanthroline derivative represented by the general formula (1) and a light emitting material other than the 1,10-phenanthroline derivative represented by the general formula (1) are used in combination, the light emission layer is represented by the general formula (1). The ratio of the 1,10-phenanthroline derivative is adjusted to 0.01 to 99.9% by weight. Preferably, it is 50 to 99.9% by weight.

The light-emitting layer can also be formed of a host material and a guest material (dopant) [Appl. Phys. Lett. , 65 , 3610 (1989)]. The 1,10-phenanthroline derivative represented by the general formula (1) can be used as a host material of the light emitting layer or as a guest material.

  When the 1,10-phenanthroline derivative represented by the general formula (1) is used as the host material of the light emitting layer, examples of the guest material include light emitting materials other than the 1,10-phenanthroline derivative. The guest material is preferably 0.01 to 40% by weight, more preferably 0.1 to 20% by weight with respect to the 1,10-phenanthroline derivative represented by the general formula (1) as the host material. It is.

  When the 1,10-phenanthroline derivative represented by the general formula (1) is used as a guest material for the light emitting layer, examples of the host material include light emitting materials other than the 1,10-phenanthroline compound. The 1,10-phenanthroline derivative represented by the general formula (1) which is a guest material is preferably 0.01 to 40% by weight, more preferably 0.1 to 20% by weight with respect to the host material. It is. The guest material may be used alone or in combination with a plurality of materials.

  As a material for the electron transport layer and the electron injection layer of the organic electroluminescence device of the present invention, a 1,10-phenanthroline derivative represented by the general formula (1) of the present invention is preferable. The organic electroluminescent element of the present invention may contain a reducing dopant in a region for transporting electrons or an interface region between the cathode and the organic layer. Moreover, the organic electroluminescent element of the present invention may contain a reducing dopant in addition to the 1,10-phenanthroline derivative represented by the general formula (1). A reducing dopant is a substance capable of reducing an electron transporting compound, for example, alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkali metal organometallic complex, alkaline earth. Metal oxides, alkaline earth metal halides, alkaline earth metal organometallic complexes, rare earth metal oxides, rare earth metal halides, rare earth metal organometallic complexes, and the like.

  Specific preferred reducing dopants include at least one alkali metal selected from lithium, sodium, potassium, rubidium, and cesium, or at least one alkaline earth metal selected from calcium, strontium, and barium. . Of these, lithium, sodium, and cesium are more preferable. More preferably, it is cesium. The reducing dopant doped into the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention is preferably adjusted to 1 to 50% by weight with respect to the 1,10-phenanthroline compound. More preferably, it is 1 to 35% by weight. By doping these alkali metals into the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention in the electron injection region, the driving voltage of the organic electroluminescence device is lowered, the emission luminance is improved, Long life can be achieved.

  In the organic electroluminescent element of the present invention, an electron injection layer composed of an insulator may be further provided between the cathode and the organic layer for the purpose of further improving the electron injection property. As the insulator used here, it is preferable to use at least one metal compound selected from alkali metal halides and alkaline earth metal halides. Examples of the alkali metal halide include lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, and lithium chloride. Examples of the alkaline earth metal halide include magnesium fluoride, calcium fluoride, barium fluoride, and strontium fluoride.

  The formation method of the hole transport layer, the light emitting layer, and the electron transport layer is not particularly limited. For example, a vacuum deposition method, an ionization deposition method, or a solution coating method (for example, a spin coating method, a casting method, or an ink jet method) can be used. Moreover, you may use together a vacuum evaporation method and a solution coating method.

When forming each layer such as a hole transport layer, a light emitting layer, and an electron transport layer by a vacuum deposition method, the vacuum deposition conditions are not particularly limited. Usually, under a vacuum of about 10 ⁻⁵ Torr or less, a boat temperature (deposition source temperature) of about 50 to 500 ° C., a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.01 to 50 nm / second. Vapor deposition is preferred. Moreover, it is preferable to form each layer of a positive hole transport layer, a light emitting layer, and an electron carrying layer continuously under vacuum. When each of the hole transport layer, the light emitting layer, and the electron transport layer is formed using a plurality of compounds, it is preferable to co-evaporate each boat containing the compounds while controlling the temperature.

  When each layer is formed by a solution coating method, components constituting each layer are dissolved or dispersed in a solvent to obtain a coating solution. Solvents include hydrocarbon solvents (eg, heptane, toluene, xylene, etc.), ketone solvents (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), halogen solvents (eg, dichloromethane, chloroform, chlorobenzene, dichlorobenzene, etc.) ), Ester solvents (eg, ethyl acetate, butyl acetate, etc.), alcohol solvents (eg, methanol, ethanol, butanol, methyl cellosolve, ethyl cellosolve, etc.), ether solvents (dibutyl ether, tetrahydrofuran, 1,4-dioxane) , 1,2-dimethoxyethane, etc.), aprotic solvents (N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, etc.), water and the like. The solvent may be used alone or a plurality of solvents may be used in combination.

  The thickness of each layer such as the hole transport layer, the light emitting layer, and the electron transport layer is not particularly limited, but is usually set to 5 to 5,000 nm.

  The organic electroluminescent element of the present invention can be protected by providing a protective layer (sealing layer) for the purpose of blocking contact with oxygen, moisture or the like, or by enclosing the element in an inert substance. Examples of the inert substance include paraffin, silicon oil, and fluorocarbon. Examples of the material used for the protective layer include fluorine resin, epoxy resin, silicone resin, polyester, polycarbonate, and photocurable resin.

  The organic electroluminescent element of the present invention can be usually used as a direct current drive type element. When a DC voltage is applied, light emission is observed when a voltage of about 1.5 to 20 V is applied with the positive polarity of the anode and the negative polarity of the cathode. Moreover, the organic electroluminescent element of this invention can be used also as an alternating current drive type | mold element. When an AC voltage is applied, light is emitted when the anode is in the + state and the cathode is in the-state. The organic electroluminescent element of the present invention includes, for example, a flat light emitter such as an electrophotographic photosensitive member and a flat panel display, a copying machine, a printer, a backlight of a liquid crystal display, a light source such as instruments, various light emitting elements, various display elements, It can be used for various labels, various sensors, various accessories, and the like.

The 1,10-phenanthroline derivative of the present invention has a much higher electron transport performance than previously known electron transport materials. For this reason, it became possible to provide materials suitable for organic semiconductor devices such as organic electroluminescent elements and organic semiconductor transistors. In addition, by using the 1,10-phenanthroline derivative of the present invention, the organic electroluminescence can operate at a driving voltage lower than that of a conventional organic electroluminescent device, has excellent light emission characteristics, and has a long life. An element can be provided. Therefore, the 1,10-phenanthroline derivative of the present invention is extremely important industrially.
The production method of the present invention is the only novel production method of the compound of the present invention. By this production method, compounds having various substituents and functional groups at various positions as shown in the structural formula of claim 1 can be obtained. I was able to get it.

  Hereinafter, specific examples of the production of the 1,10-phenanthroline derivative represented by the general formula (1) of the present invention and the production of an organic electroluminescent device using the compound will be exemplified. It is not limited at all by an example.

８−アミノ−７−ベンゾイルキノリン（１．２４ｇ、５ｍｍｏｌ）と５−フェニル−２Ｈ−アセナフチレン−１−オン（１．４６ｇ、６ｍｍｏｌ）の酢酸（１０ｍＬ）溶液に濃硫酸（０．５ｍＬ）を加えた。反応混合物を加熱還流下で１５時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をトルエンから再結晶して３，１４−ジフェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．０ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝４５６，Ｍ^＋）で同定した。 Example 1 Production of Compound {3,14-Diphenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-229

Concentrated sulfuric acid (0.5 mL) was added to a solution of 8-amino-7-benzoylquinoline (1.24 g, 5 mmol) and 5-phenyl-2H-acenaphthylene-1-one (1.46 g, 6 mmol) in acetic acid (10 mL). It was. The reaction mixture was stirred for 15 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystals were recrystallized from toluene to obtain 3,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline (1.0 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 456, M ⁺ ).

８−アミノ−７−（１−ナフトイル）キノリン（１．７９ｇ、６ｍｍｏｌ）と５−フェニル−２Ｈ−アセナフチレン−１−オン（１．７６ｇ、７．２ｍｍｏｌ）の酢酸（２０ｍＬ）溶液に濃硫酸（０．６ｍＬ）を加えた。反応混合物を加熱還流下で１３時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をシリカゲルカラムクロマトグラフィーで精製したのち、トルエンから再結晶して１４−（１−ナフチル）−３−フェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（２．１ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝５０６，Ｍ^＋）で同定した。 Example 2 Production of Compound {14- (1-naphthyl) -3-phenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-230

To a solution of 8-amino-7- (1-naphthoyl) quinoline (1.79 g, 6 mmol) and 5-phenyl-2H-acenaphthylene-1-one (1.76 g, 7.2 mmol) in acetic acid (20 mL) was added concentrated sulfuric acid (20 mL). 0.6 mL) was added. The reaction mixture was stirred for 13 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystals were purified by silica gel column chromatography and then recrystallized from toluene to give 14- (1-naphthyl) -3-phenylacenaphtho [1,2-b] [1,10] phenanthroline (2.1 g). Obtained. The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 506, M ⁺ ).

８−アミノ−７−ベンゾイル−３−フェニルキノリン（１．９５ｇ、６ｍｍｏｌ）と２Ｈ−アセナフチレン−１−オン（１．１１ｇ、６．６ｍｍｏｌ）の酢酸（３０ｍＬ）溶液に濃硫酸（０．６ｍＬ）を加えた。反応混合物を加熱還流下で３．５時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をトルエンから再結晶して１０，１４−ジフェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．９ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝４５６，Ｍ^＋）で同定した。 Example 3 Production of Compound {10,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-291

Concentrated sulfuric acid (0.6 mL) in a solution of 8-amino-7-benzoyl-3-phenylquinoline (1.95 g, 6 mmol) and 2H-acenaphthylene-1-one (1.11 g, 6.6 mmol) in acetic acid (30 mL) Was added. The reaction mixture was stirred for 3.5 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystals were recrystallized from toluene to obtain 10,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline (1.9 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 456, M ⁺ ).

８−アミノ−７−ベンゾイル−３−（１−ナフチル）キノリン（１．８７ｇ、５ｍｍｏｌ）と２Ｈ−アセナフチレン−１−オン（０．９３ｇ、５．５ｍｍｏｌ）の酢酸（１０ｍＬ）溶液に濃硫酸（０．５ｍＬ）を加えた。反応混合物を加熱還流下で２２時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をＮ，Ｎ−ジメチルホルムアミドから再結晶して１０−（１−ナフチル）−１４−フェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．１ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝５０６，Ｍ^＋）で同定した。 Example 4 Production of Compound {10- (1-naphthyl) -14-phenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-292

To a solution of 8-amino-7-benzoyl-3- (1-naphthyl) quinoline (1.87 g, 5 mmol) and 2H-acenaphthylene-1-one (0.93 g, 5.5 mmol) in acetic acid (10 mL) was added concentrated sulfuric acid (10 mL). 0.5 mL) was added. The reaction mixture was stirred for 22 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystals were recrystallized from N, N-dimethylformamide to give 10- (1-naphthyl) -14-phenylacenaphtho [1,2-b] [1,10] phenanthroline (1.1 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 506, M ⁺ ).

８−アミノ−７−ベンゾイル−４−フェニルキノリン（１．９５ｇ、６ｍｍｏｌ）と２Ｈ−アセナフチレン−１−オン（１．１１ｇ、６．６ｍｍｏｌ）の酢酸（１２ｍＬ）溶液に濃硫酸（０．６ｍＬ）を加えた。反応混合物を加熱還流下で４時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をトルエンから二度再結晶して１１，１４−ジフェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．９ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝４５６，Ｍ^＋）で同定した。 Example 5 Production of Compound {11,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-303

Concentrated sulfuric acid (0.6 mL) in a solution of 8-amino-7-benzoyl-4-phenylquinoline (1.95 g, 6 mmol) and 2H-acenaphthylene-1-one (1.11 g, 6.6 mmol) in acetic acid (12 mL) Was added. The reaction mixture was stirred for 4 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystal was recrystallized twice from toluene to obtain 11,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline (1.9 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 456, M ⁺ ).

８−アミノ−７−ベンゾイル−３−フェニルキノリン（１．９５ｇ、６ｍｍｏｌ）と５−フェニル−２Ｈ−アセナフチレン−１−オン（１．７６ｇ、７．２ｍｍｏｌ）の酢酸（２０ｍＬ）溶液に濃硫酸（０．６ｍＬ）を加えた。反応混合物を加熱還流下で９時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をＮ，Ｎ−ジメチルホルムアミドから再結晶して３，１０，１４−トリフェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（２．３ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝５３２，Ｍ^＋）で同定した。 Example 6 Production of Compound {3,10,14-Triphenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-397

To a solution of 8-amino-7-benzoyl-3-phenylquinoline (1.95 g, 6 mmol) and 5-phenyl-2H-acenaphthylene-1-one (1.76 g, 7.2 mmol) in acetic acid (20 mL) was added concentrated sulfuric acid (20 mL). 0.6 mL) was added. The reaction mixture was stirred for 9 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystal was recrystallized from N, N-dimethylformamide to obtain 3,10,14-triphenylacenaphtho [1,2-b] [1,10] phenanthroline (2.3 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 532, M ⁺ ).

８−アミノ−７−ベンゾイル−３−（１−ナフチル）キノリン（１．５０ｇ、４ｍｍｏｌ）と５−フェニル−２Ｈ−アセナフチレン−１−オン（１．１７ｇ、４．８ｍｍｏｌ）の酢酸（８ｍＬ）溶液に濃硫酸（０．４ｍＬ）を加えた。反応混合物を加熱還流下で２２時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をジメチルスルホキシドから再結晶して１０−（１−ナフチル）−３，１４−ジフェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．６ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝５８２，Ｍ^＋）で同定した。 Example 7 Production of Compound {10- (1-naphthyl) -3,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-398

A solution of 8-amino-7-benzoyl-3- (1-naphthyl) quinoline (1.50 g, 4 mmol) and 5-phenyl-2H-acenaphthylene-1-one (1.17 g, 4.8 mmol) in acetic acid (8 mL) To the mixture was added concentrated sulfuric acid (0.4 mL). The reaction mixture was stirred for 22 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystals were recrystallized from dimethyl sulfoxide to obtain 10- (1-naphthyl) -3,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline (1.6 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 582, M ⁺ ).

８−アミノ−７−ベンゾイル−４−フェニルキノリン（１．９５ｇ、６ｍｍｏｌ）と５−フェニル−２Ｈ−アセナフチレン−１−オン（１．７６ｇ、７．２ｍｍｏｌ）の酢酸（２０ｍＬ）溶液に濃硫酸（０．６ｍＬ）を加えた。反応混合物を加熱還流下で２２時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をトルエンから再結晶して３，１１，１４−トリフェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（２．５ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝５３２，Ｍ^＋）で同定した。 Example 8 Production of Compound {3,11,14-triphenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound Nos. 1-413

To a solution of 8-amino-7-benzoyl-4-phenylquinoline (1.95 g, 6 mmol) and 5-phenyl-2H-acenaphthylene-1-one (1.76 g, 7.2 mmol) in acetic acid (20 mL) was added concentrated sulfuric acid (20 mL). 0.6 mL) was added. The reaction mixture was stirred for 22 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystal was recrystallized from toluene to obtain 3,11,14-triphenylacenaphtho [1,2-b] [1,10] phenanthroline (2.5 g). The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 532, M ⁺ ).

８−アミノ−７−ベンゾイルキノリン（１．２４ｇ、５ｍｍｏｌ）と５−ブロモ−２Ｈ−アセナフチレン−１−オン（１．４８ｇ、６ｍｍｏｌ）の酢酸（１０ｍＬ）溶液に濃硫酸（０．５ｍＬ）を加えた。反応混合物を加熱還流下で１３時間撹拌した。冷却後、反応混合物を過剰の５％アンモニア水溶液に投入して塩基性にした。生成した沈殿を濾別し、乾燥した。粗結晶をトルエンから再結晶して例示化合物番号１−２４２の化合物である３−ブロモ−１４−フェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（２．１ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝４５８，Ｍ^＋）で同定した。
次いで、例示化合物番号１−２４２の化合物である３−ブロモ−１４−フェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．８４ｇ、４ｍｍｏｌ）、ジフェニルアミン（１．０２ｇ、６ｍｍｏｌ）、トリス（ジベンジリデンアセトン）二パラジウム（０．１１ｇ、０．１２ｍｍｏｌ）、ジ−ｔｅｒｔ−ブチル（２−ビフェニリル）ホスフィン（１５８ｍｇ、０．４８ｍｍｏｌ）、ナトリウムｔｅｒｔ−ブトキシド（０．５８ｇ、６ｍｍｏｌ）のテトラヒドロフラン（２０ｍＬ）懸濁液を２２時間、加熱還流した。冷却後、反応混合物に水を加え、クロロホルムで抽出した。溶媒を留去して得られる粗結晶をトルエンから再結晶して、例示化合物番号１−２４１の化合物である３−（ジフェニルアミノ）−１４−フェニルアセナフト［１，２−ｂ］［１，１０］フェナントロリン（１．３ｇ）を得た。化学構造は^１Ｈ−ＮＭＲスペクトル、マススペクトル（ｍ／ｅ＝５４７，Ｍ^＋）で同定した。 Example 9 Production of Compound {3- (diphenylamino) -14-phenylacenaphtho [1,2-b] [1,10] phenanthroline} of Exemplified Compound No. 1-241

Concentrated sulfuric acid (0.5 mL) was added to a solution of 8-amino-7-benzoylquinoline (1.24 g, 5 mmol) and 5-bromo-2H-acenaphthylene-1-one (1.48 g, 6 mmol) in acetic acid (10 mL). It was. The reaction mixture was stirred for 13 hours under heating to reflux. After cooling, the reaction mixture was made basic by pouring into excess 5% aqueous ammonia. The formed precipitate was filtered off and dried. The crude crystals were recrystallized from toluene to obtain 3-bromo-14-phenylacenaphtho [1,2-b] [1,10] phenanthroline (2.1 g), which is the compound of Exemplified Compound No. 1-242. The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 458, M ⁺ ).
Subsequently, 3-bromo-14-phenylacenaphtho [1,2-b] [1,10] phenanthroline (1.84 g, 4 mmol) and diphenylamine (1.02 g, 6 mmol) which are the compounds of Exemplified Compound No. 1-224 , Tris (dibenzylideneacetone) dipalladium (0.11 g, 0.12 mmol), di-tert-butyl (2-biphenylyl) phosphine (158 mg, 0.48 mmol), sodium tert-butoxide (0.58 g, 6 mmol) The tetrahydrofuran (20 mL) suspension was heated to reflux for 22 hours. After cooling, water was added to the reaction mixture and extracted with chloroform. The crude crystals obtained by distilling off the solvent were recrystallized from toluene to give 3- (diphenylamino) -14-phenylacenaphtho [1,2-b] [1, which is a compound of Exemplified Compound No. 1-241. 10] Phenanthroline (1.3 g) was obtained. The chemical structure was identified by ¹ H-NMR spectrum and mass spectrum (m / e = 547, M ⁺ ).

Example 10 Production of Organic Electroluminescent Device [ITO (150 mm) / α-NPD (40 nm) / Alq3 (30 nm) / Exemplary Compound No. 1-230 Compound (30 nm) / LiF (0.2 nm) / Al (150 nm)] (Evaluation of electron transport performance)
A glass substrate having a size of 25 mm × 25 mm having an ITO transparent electrode having a thickness of 150 nm was ultrasonically cleaned using acetone, a cleaning agent (trade name: Semico Clean 56), and isopropanol. Subsequently, after boiling in isopropanol, the substrate washed with UV / ozone was used as a transparent conductive support substrate. This glass substrate was placed in a vacuum deposition apparatus, and N, N'-di (1-naphthyl) -N, N'-diphenyl-4,4'-diaminobiphenyl (α -NPD) was deposited to a thickness of 40 nm, and then tris (8-hydroxyquinolinato) aluminum (Alq3) represented by the following formula was deposited to a thickness of 30 nm as a light emitting layer. Subsequently, the compound of exemplary compound number 1-230 was vapor-deposited as a 30 nm thickness as an electron carrying layer. On top of this, lithium fluoride was deposited to a thickness of 0.2 nm, and then aluminum was deposited as an electrode to a thickness of 150 nm to produce an organic electroluminescent device. When a DC voltage of 6.0 V is applied to this element, yellow-green light emission from Alq3 is obtained with a current density of 121.7 mA / cm ² , an emission luminance of 2,993 cd / m ² , and a current efficiency of 2.46 cd / A. It was.

Examples 11-17 Preparation of organic electroluminescent element (evaluation of electron transport performance)
In Example 10, instead of using the compound of Exemplified Compound No. 1-230 for the electron transport layer, the compound of Exemplified Compound No. 1-229 (Example 11), the compound of Exemplified Compound No. 1-291 (Example 12) Example Compound No. 1-292 (Example 13), Example Compound No. 1-303 Compound (Example 14), Example Compound No. 1-397 Compound (Example 15), Example Compound No. 1-398 An organic electroluminescent device was produced according to the procedure described in Example 10, except that the compound (Example 16) and the compound of Example Compound Nos. 1-413 (Example 17) were used. From each element, yellow-green light emission from Alq3 was obtained. Table 3 shows the results of examining the characteristics (current density, light emission luminance, and current efficiency at a DC applied voltage of 6.0 V). From this table, it can be seen that the 1,10-phenanthroline derivative exhibits higher electron transport performance than Alq3. In particular, the device using the compound of Exemplified Compound No. 1-230 shown in Example 10 has a current density and emission luminance about 10 times that of Alq3.

Comparative Example 1
In Example 10, an organic electroluminescent element was produced according to the procedure described in Example 10, except that Alq3 was used instead of the compound of Exemplified Compound No. 1-230 in the electron transport layer. From this device, yellow-green light emission from Alq3 was obtained. Table 3 shows the results of examining the characteristics (current density, light emission luminance, and current efficiency at a DC applied voltage of 6.0 V).

Example 18 Production of Organic Electroluminescent Device [ITO (150 mm) / α-NPD (40 nm) / Exemplary Compound No. 1-241 Compound (60 nm) / LiF (0.2 nm) / Al (150 nm)] (Electron Transport Performance and Evaluation of luminous performance)
A 40 mm × 40 mm glass substrate having an ITO transparent electrode having a thickness of 150 nm was ultrasonically cleaned using acetone, a cleaning agent (trade name: Semicoclean 56), and isopropanol. Subsequently, after boiling in isopropanol, the substrate washed with UV / ozone was used as a transparent conductive support substrate. This glass substrate was placed in a vacuum deposition apparatus, and N, N′-di (1-naphthyl) -N, N′-diphenyl-4,4′-diaminobiphenyl (α-NPD) was 40 nm as a hole transport layer. Then, the compound of Exemplified Compound No. 1-241 was deposited to a thickness of 60 nm as a light emitting layer / electron transport layer. On top of this, lithium fluoride was deposited to a thickness of 0.2 nm, and then aluminum was deposited as an electrode to a thickness of 150 nm to produce an organic electroluminescent device. When a DC voltage of 6.0 V was applied to this device, the current density was 53.2 mA / cm ² , the luminance was 1,745 cd / m ² , and the current efficiency was 3.28 cd / A. A yellow luminescence was obtained. From a comparison between this evaluation result and Comparative Example 1, it can be seen that the compound of Exemplified Compound No. 1-241 has extremely high electron transport performance and light emitting function.

Example 19 Preparation of Organic Electroluminescent Device [ITO (150 mm) / α-NPD (40 nm) / Alq3 (30 nm) / Exemplary Compound No. 1-241 Compound: Cesium (30 nm) / Al (150 nm)] Effect of reducing dopant on
A 40 mm × 40 mm glass substrate having an ITO transparent electrode having a thickness of 150 nm was ultrasonically cleaned using acetone, a cleaning agent (trade name: Semicoclean 56), and isopropanol. Subsequently, after boiling in isopropanol, the substrate washed with UV / ozone was used as a transparent conductive support substrate. This glass substrate was placed in a vacuum deposition apparatus, and N, N′-di (1-naphthyl) -N, N′-diphenyl-4,4′-diaminobiphenyl (α-NPD) was 40 nm as a hole transport layer. Then, tris (8-hydroxyquinolinato) aluminum (Alq3) was evaporated to a thickness of 30 nm as a light emitting layer. Next, the compound of Exemplified Compound No. 1-241 and the reducing dopant cesium (cesium source: manufactured by SAES Getters Co., Ltd., cesium dispenser) were co-deposited to a film thickness of 30 nm as the electron transport layer (Compound of Exemplified Compound No. 1-241) : Cesium weight ratio 6: 1). On top of this, aluminum was deposited as an electrode to a thickness of 150 nm to produce an organic electroluminescent device. When a DC voltage of 6.0 V is applied to this element, yellow-green light emission from Alq3 is obtained with a current density of 337.5 mA / cm ² , an emission luminance of 8,541 cd / m ² , and a current efficiency of 2.53 cd / A. It was. When this element was used to drive at a constant current at an initial luminance of 1,000 cd / m ² , the time during which the luminance was reduced by half (half life) was 1,300 hours.

Examples 20-23 Preparation of organic electroluminescent device (effect of reducing dopant on electron transport performance)
In Example 19, instead of using the compound of exemplary compound number 1-241 for the electron transport layer, the compound of exemplary compound number 1-229 (Example 20) and the compound of exemplary compound number 1-230 (Example 21) An organic electroluminescent device was prepared according to the procedure described in Example 19 except that the compound of Exemplified Compound No. 1-303 (Example 22) and the compound of Exemplified Compound No. 1-397 (Example 23) were used. . From these elements, yellow-green light emission from Alq3 was obtained. Table 4 shows a comparison of the results of investigating the characteristics of these elements (current density, light emission luminance, current efficiency at a DC applied voltage of 6.0 V) and results when no reducing dopant is used. From this table, it can be seen that the electron transport performance of the 1,10-phenanthroline derivative represented by the general formula (1) is drastically improved by doping with cesium.

Comparative Example 2
In Example 19, instead of using the compound of Exemplified Compound No. 1-241 for the electron transport layer, an organic electroluminescent device was produced according to the operation described in Example 19 except that Alq3 was used. From this device, yellow-green light emission from Alq3 was obtained. Table 4 shows the results of examining the characteristics (current density, light emission luminance, and current efficiency at a DC applied voltage of 6.0 V).

¹ shows the ¹ H-NMR spectrum of Compound No. 1-291 (10,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline) obtained in Example 3. The mass spectrum of the compound (10,14-diphenylacenaphtho [1,2-b] [1,10] phenanthroline) of exemplary compound number 1-291 obtained in Example 3 is shown. 10 is a graph showing the relationship between the current density and voltage of the organic electroluminescent element produced in Example 10 together with Comparative Example 1. 6 is a graph showing the relationship between the light emission luminance and voltage of the organic electroluminescent element produced in Example 10 together with Comparative Example 1. FIG. 14 is a graph showing the relationship between the current density and voltage of an organic electroluminescent element produced in Example 23 together with Example 15. FIG. 14 is a graph showing the relationship between the light emission luminance and the voltage of the organic electroluminescent element produced in Example 23 together with Example 15. FIG.

Claims (12)

The following general formula (1)

(Wherein R ^{1 to} R ¹² are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group) An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 To 40 diarylamino groups, substituted or unsubstituted arylheteroarylamino groups having 10 to 40 carbon atoms, substituted or unsubstituted alkylaryl groups having 7 to 40 carbon atoms Arylamino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹ to R ¹² are bonded with a substituent group among adjacent respectively To form a ring structure.)
A 1,10-phenanthroline derivative represented by: The following general formula (2)

Wherein R ^{7 to} R ¹¹ are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 To 40 diarylamino groups, substituted or unsubstituted arylheteroarylamino groups having 10 to 40 carbon atoms, substituted or unsubstituted alkylaryl groups having 7 to 40 carbon atoms Arylamino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹² represents a hydrogen atom, a substituted or unsubstituted 1 to carbon atoms 20 alkyl groups, perfluoroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 45 carbon atoms, substituted or unsubstituted carbons A heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, substituted or An unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, a substituted or unsubstituted carbon number 10 A group selected from the group consisting of 40 arylheteroarylamino groups, substituted or unsubstituted alkylarylamino groups having 7 to 40 carbon atoms, substituted or unsubstituted alkylheteroarylamino groups having 5 to 40 carbon atoms, Yes; R ^{7 to} R ¹² may be bonded together by adjacent substituents to form a cyclic structure.
And an amino derivative represented by the following general formula (3)

(In the formula, R ^{1 to} R ⁶ are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 -40 diarylamino group, substituted or unsubstituted arylheteroarylamino group having 10 to 40 carbon atoms, substituted or unsubstituted alkyl aryl having 7 to 40 carbon atoms Amino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹ to R ⁶ are bonded with a substituent group among adjacent respectively To form a ring structure.)
A reaction with an α-methylenecarbonyl compound represented by the following general formula (1):

(Wherein R ^{1 to} R ¹² are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a perfluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group) An alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, an organosilicon group having 3 to 40 carbon atoms, a substituted or An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted dialkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 12 To 40 diarylamino groups, substituted or unsubstituted arylheteroarylamino groups having 10 to 40 carbon atoms, substituted or unsubstituted alkylaryl groups having 7 to 40 carbon atoms Arylamino group, are each independently a group selected from the group consisting of alkyl heteroarylamino groups, substituted or unsubstituted 5 to 40 carbon atoms; R ¹ to R ¹² are bonded with a substituent group among adjacent respectively To form a ring structure.)
The manufacturing method of the 1,10-phenanthroline derivative of Claim 1 shown by these.   An electron transport material comprising a 1,10-phenanthroline derivative represented by the general formula (1).   An electron injection material comprising a 1,10-phenanthroline derivative represented by the general formula (1).   A light emitting material comprising a 1,10-phenanthroline derivative represented by the general formula (1).   An organic electroluminescence device comprising a layer containing at least one 1,10-phenanthroline derivative represented by the general formula (1) between a pair of electrodes.   The organic electroluminescent device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is an electron transport layer.   The organic electroluminescent device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is an electron injection layer.   The organic electroluminescent device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is a light emitting layer.   The organic electroluminescence device according to claim 6, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) is doped with an alkali metal.   The organic electroluminescence device according to claim 10, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) doped with an alkali metal is an electron transport layer. The organic electroluminescence device according to claim 10, wherein the layer containing the 1,10-phenanthroline derivative represented by the general formula (1) doped with an alkali metal is an electron injection layer.

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