JP4700442B2 - A phenazacillin derivative, a hole transport material comprising the same, a hole injection material, a light emitting layer host material, and an organic EL device including the same. - Google Patents

Description

  The present invention relates to a phenazacillin derivative, a hole transport material comprising the same, a hole injection material, a light emitting layer host material, and an organic EL device including the same.

In 1987, Kodak's C.I. After being reported in Non-Patent Document 1 by W, Tang et al., Organic EL has come into the limelight, and research has been actively conducted as a new technology.
The excellent point of the organic EL developed by Tang et al. Is that the charge transporting portion and the light emitting functional portion are separated, thereby enabling low voltage driving and high efficiency of the organic EL element.
In addition, as one of the means for improving the durability of such an element that can sufficiently withstand the high efficiency, low voltage drive, or use of the organic EL element, research on a multi-layer laminated element provided with a charge injection layer is also advanced. ing. Specifically, a general method is to provide a hole injection layer on an ITO substrate, a hole transport layer thereon, and further laminate a light emitting layer, an electron transport layer, an electron injection layer, and a cathode in that order. is there. In such an element, charges are smoothly injected from the electrodes, and holes and electrons are easily recombined in the light emitting layer.
As a material used for the electron injection layer, a material containing lithium metal is generally used, for example, a metal lithium, a lithium complex of 8-hydroxyquinoline, or a material in which 1,10-phenanthridine is doped with lithium.
On the other hand, the material used for the hole transport layer is a low molecular weight material copper phthalocyanine (CuPc), and the polymer material is a polyarinine-polystyrene sulfonic acid (Pani-PSS) or polyethylenedioxathiophene-polystyrene sulfonic acid (PEDOT-). PSS) is used.
However, in the case of copper phthalocyanine, since this absorbs red light emission, it cannot be said that a combination with a red light emitting material is appropriate. In the case of the polymer materials described above, these are formed from an aqueous solvent by spin coating. After film formation, high temperature and high vacuum conditions are required to completely remove moisture, so that it is not always possible to produce the best element for an organic EL element that is sensitive to moisture.
Therefore, in order to produce a high-performance organic EL, it was necessary to develop a new hole injection material capable of overcoming these weak points.
In the past, studies on polymers using a phenazacillin skeleton have been reported in Patent Documents 1 to 3 and Non-Patent Documents 2 to 3, and it has been confirmed that the phenazacillin skeleton exhibits hole transport performance.
The inventors of the present application last year stiffened the central skeleton for the purpose of improving Tg (improving heat resistance) because the Tg of the synthesized hole transport material having a tetraphenylsilane skeleton is not so high as around 90-100 ° C. Therefore, it was crosslinked with an N-methyl group, an N-phenyl group or the like (a compound having a crosslinked central skeleton is a phenazacillin derivative). As a result, Tg was improved to 100 to 120 ° C., but the energy gap was about 3.0 eV and about α-NPD (α-NPD energy gap was about 3.0 eV), and it was not a wide gap. It was difficult to apply to phosphorescent devices (can be used with fluorescent devices). Moreover, the ionization potential of the phenazacillin compound synthesized this time is as low as about 5.1 to 5.3 eV (the ionization potential of α-NPD is about 5.4 eV) (when used for a hole transport layer in a fluorescent element, the ionization potential is low). Because it is low, there is a concern about the hole injection barrier to the light emitting layer depending on the device configuration), so it was judged that it was more effective to use it as a hole injection material than to apply to the hole transport layer (actually, experiment Based on the result, the effect of the phenazacillin compound is more remarkable in the element used in the hole injection layer than in Alq and the two-layer element used in the hole injection layer).

JP 2002-275249 A JP 2002-69161 A Japanese Patent Laid-Open No. 10-218884 Appl. Phys. Lett. 1987 H. Hayashi et. al. Chem. Lett. 688 (2000) D. Wasserman et. al. J. et al. Org. Chem. , 30, 3248 (1965)

  An object of the present invention is to provide a novel phenazacillin derivative useful as a hole transport material, a hole injection material, and a light emitting layer host material in an organic EL element, and an organic EL element using the same.

〔式中、Ｒ^１ は、置換または無置換のアルキル基および置換または無置換のアリール基よりなる群から選ばれた基であり、Ｒ ^２ 、Ｒ ^３ は、置換または無置換のアリール基であり、Ｒ ^４ 、Ｒ ^５ 、Ｒ ^７ 〜Ｒ ^９ 、Ｒ ^１１ は、水素原子、ハロゲン原子、シアノ基、置換または無置換の炭素数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、置換または無置換の炭素数３〜２０のアルケニル基、置換または無置換の炭素数６〜４５のアリール基、置換または無置換の炭素数４〜４０のヘテロアリール基、炭素数３〜４０の有機ケイ素基、置換または無置換の炭素数１〜２０のアルコキシ基、置換または無置換の炭素数６〜２０のアリールオキシ基、置換または無置換の炭素数６〜２０のアリールスルホニル基、置換または無置換の炭素数２〜３０のジアルキルアミノ基、置換または無置換の炭素数１２〜４０のジアリールアミノ基、置換または無置換の炭素数８〜４０のジヘテロアリールアミノ基、置換または無置換の炭素数１０〜４０のアリールヘテロアリールアミノ基、置換または無置換の炭素数７〜４０のアルキルアリールアミノ基、置換または無置換の炭素数５〜４０のアルキルヘテロアリールアミノ基、置換または無置換の炭素数２〜３０のアルコキシカルボニル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 ^６ は、−Ｎ（Ａｒ^１、Ａｒ^２）であり、Ｒ ^１０ は、−Ｎ（Ａｒ ^１ 、Ａｒ ^２ ）又は−Ｎ（Ａｒ^３、Ａｒ^４）である。また、Ａｒ^１〜Ａｒ^４は、置換または無置換のアリール基であり、さらに、Ａｒ^１とＡｒ^２、および／またはＡｒ^３とＡｒ^４は、それぞれ一体になって置換または無置換の複素環を形成していてもよい。また、前記「置換」における置換基は、炭素数１〜４のアルキル基である。〕
本発明の第２は、請求項１記載のフェナザシリン誘導体よりなるホール輸送材料に関する。
本発明の第３は、請求項１記載のフェナザシリン誘導体よりなるホール注入材料に関する。
本発明の第４は、請求項１記載のフェナザシリン誘導体よりなる発光層ホスト材料に関する。
本発明の第５は、請求項１記載のフェナザシリン誘導体を用いたことを特徴とする有機ＥＬ素子に間する。
本発明の第６は、請求項１記載のフェナザシリン誘導体をホール輸送層、ホール注入層および発光層よりなる群から選ばれた層の少なくとも１つの層に用いたことを特徴とする有機ＥＬ素子に関する。
本発明の第７は、発光材料として燐光材料を用いたものである請求項６記載の有機ＥＬ素子に関する。 The first of the present invention relates to a phenazacillin derivative represented by the following general formula (1) .

Wherein, R ¹ is a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group or al election Barre groups consisting of group, R ^2, R ³ is a substituted or unsubstituted aryl group R ⁴ , R ⁵ , R ^{7 to} R ⁹ and R ¹¹ are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a perfluoroalkyl having 1 to 20 carbon atoms. Group, substituted or unsubstituted alkenyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 45 carbon atoms, substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, 3 to 40 carbon atoms Organic silicon group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted arylsulfonyl group having 6 to 20 carbon atoms, substituted Or Substituted dialkylamino group having 2 to 30 carbon atoms, substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, substituted or unsubstituted diheteroarylamino group having 8 to 40 carbon atoms, substituted or unsubstituted carbon A 10 to 40 arylheteroarylamino group, a substituted or unsubstituted alkylarylamino group having 7 to 40 carbon atoms, a substituted or unsubstituted alkylheteroarylamino group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon R ⁶ is a group independently selected from the group consisting of alkoxycarbonyl groups of 2 to 30, R ⁶ is —N (Ar ¹ , Ar ² ), and R ¹⁰ is —N (Ar ¹ , Ar a ²⁾ or ^{-N (Ar 3, Ar 4)} . Ar ^{1 to} Ar ⁴ are substituted or unsubstituted aryl groups, and Ar ¹ and Ar ² , and / or Ar ³ and Ar ⁴ are combined to form a substituted or unsubstituted heterocyclic ring, respectively. It may be formed. In addition, the substituent in the “substitution” is an alkyl group having 1 to 4 carbon atoms. ]
The second of the present invention relates to a hole transport material comprising the phenazacillin derivative according to claim 1.
A third aspect of the present invention relates to a hole injection material comprising the phenazacillin derivative according to claim 1.
4th of this invention is related with the light emitting layer host material which consists of a phenazacillin derivative of Claim 1.
A fifth aspect of the present invention relates to an organic EL device using the phenazacillin derivative according to claim 1.
A sixth aspect of the present invention relates to an organic EL device characterized in that the phenazacillin derivative according to claim 1 is used in at least one layer selected from the group consisting of a hole transport layer, a hole injection layer, and a light emitting layer. .
The seventh aspect of the present invention relates to the organic EL device according to claim 6, wherein a phosphorescent material is used as the light emitting material.

  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 Le 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- -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 -Naphtyl group, o-tolyl group, m-tolyl group, p-tolyl group, p-tert-butylphenyl group, 4-methoxyphenyl group, 4-fluorophenyl group, 4-dimethylaminophenyl group, 4-cyanophenyl Group, 4-trifluorophenyl group, 4-methyl-1-naphthyl group, 4-phenyl-1-naphthyl group, 2-methoxy-1-naphthyl group, 10-methyl-9-anthryl group, 10-methoxy -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, 3 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) ) A methyl group and the like can be mentioned.

  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 group 4-phenyl-2-quinolyl group, 2-quinoxalinyl group, 2-quinazolinyl group, 4-quinazolinyl group, 5-quinazolinyl group, 6-quinazolinyl group, 1,8-naphthyridin-2-yl 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-phenanthroline-4-yl group, 3-phenyl-1,10-phenyl group Nantrolin-5-yl group, 4-phenyl-1,10-phenanthrolin-2-yl group, 4-phenyl-1,10-phenanthrolin-3-yl group, 4-phenyl-1,10-phenanthroline-5-yl Group, 4,7-diphenyl-1,10-phenanthroline-2-yl group, 4-phenyl-1,10-phenanthroline-3-yl group, 1,8-phenanthroline-2-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-phenanthroline-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 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-methylindol-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, dibenzothiophen-3-yl group, dibenzothiophen-4-yl group, 9-phenylcarbazol-2-yl 9-phenylcarbazol-3-yl group, 9-methylcarbazol-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-butyl Ruhexyloxy 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-dimethylphenyl Oren-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 Enyloxy group, 4-fluorophenyloxy group, 4-dimethylaminophenyloxy group, 4-cyanophenyloxy group, 4-trifluorophenyloxy group, 4-methyl-1-naphthyloxy group, 4-phenyl-1-naphthyl Oxy group, 2-methoxy-1-naphthyloxy group, 10-methyl-9-anthryloxy group, 10-methoxy-9-anthryloxy group, 4-phenyl-8-fluoranthenyloxy group, 7-dimethyl Amino-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-pyridyl group Oxy 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-phenanthridi Ruoxy 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 arylsulfonyl group having 6 to 20 carbon atoms include phenylsulfonyl group, 1-naphthylsulfonyl group, 2-naphthylsulfonyl group, 4-phenyl-1-naphthylsulfonyl group, 1-anthrylsulfonyl group, 2-anthrylsulfonyl group, 9-anthrylsulfonyl group, 10-phenyl-9-anthrylsulfonyl group, 1-phenanthrylsulfonyl group, 2-phenanthrylsulfonyl group, 3-phenanthrylsulfonyl group, 4 -Phenanthrylsulfonyl group, 9-phenanthrylsulfonyl group, 1-pyrenylsulfonyl group, 2-pyrenylsulfonyl group, 2-perylenylsulfonyl group, 3-perylenylsulfonyl group, 3-fluoranthenyl Sulfonyl group, 8-Fluoranthenylsulfonyl group, 2-Triphenylenylsulfur Nyl group, 9,9-dimethylfluoren-2-ylsulfonyl group, 9,9-dibutylfluoren-2-ylsulfonyl group, 9,9-dihexylfluoren-2-ylsulfonyl group, 9,9-dioctylfluorene-2 -Ylsulfonyl group, 9,9-diphenylfluoren-2-ylsulfonyl group, 2-biphenylylsulfonyl group, 3-biphenylylsulfonyl group, 4-biphenylylsulfonyl group, p-terphenyl-3-ylsulfonyl group, p-terphenyl-4-ylsulfonyl group, m-terphenyl-3-ylsulfonyl group, m-terphenyl-4-ylsulfonyl group, o-terphenyl-3-ylsulfonyl group, o-terphenyl-4 -Ylsulfonyl group, 4- (1-naphthyl) -1-naphthylsulfonyl group, o-tolylsulfonyl 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, di Chlohexylamino, methyloctylamino, heptylmethylamino, heptylisopropylamino, diheptylamino, methyloctylamino, octylpropylamino, dioctylamino, decylethylamino, decylisopropylamino, di Examples include (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- (1 Anthryl) phenylamino group, N- (2-anthryl) -N-phenylamino group, N- (9-anthryl) -N-phenylamino group, N- (10-methyl-9-anthryl) -N-phenylamino Group, N- (1-anthryl) -N- (1-naphthyl) amino group, N- (2-anthryl) -N- (1-naphthyl) amino group, N- (9-anthryl) -N- (2 -Naphtyl) 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-dimethyl) Fluoren-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) amino 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-anthryl) ) -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-fluorane) Tenenyl) -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 group N- (1-anthryl) -N- (3-perylenyl) amino 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 can be mentioned.

Examples of the substituted or unsubstituted diheteroarylamino group having 8 to 40 carbon atoms include an N, N-di (2-furyl) amino group, an N, N-di (2-thienyl) amino group, and an N, N-di group. (2-pyridyl) amino group, N, N-di (3-pyridyl) amino group, N, N-di (4-pyridyl) amino group, N- (2-pyridyl) -N- (4-pyridyl) amino Group, N- (2-furyl) -N- (2-pyridyl) amino group, N- (2-pyridyl) -N- (2-thienyl) amino group, N, N-di (benzo [b] furan- 2-yl) amino group, N- (benzo [b] furan-2-yl) -N- (2-pyridyl) amino group, N- (benzo [b] furan-2-yl) -N- (2- Furyl) amino group, N- (benzo [b] furan-2-yl) -N- (2-thienyl) amino group, N, N-di ( Nzo [b] thiophen-2-yl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-pyridyl) amino group, N- (benzo [b] thiophen-2-yl ) -N- (2-furyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-thienyl) amino group, N, N-di (1-methylindol-2-yl) ) Amino group, N- (1-methylindol-2-yl) -N- (2-pyridyl) amino group, N- (2-furyl) -N- (1-methylindol-2-yl) amino group, N- (1-methylindol-2-yl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N- (1-methylindol-2-yl) amino The group N- (benzo [b] thiophen-2-yl) -N- (1-methyli Dole-2-yl) amino group, N, N-di (dibenzofuran-2-yl) amino group, N, N-di (dibenzofuran-3-yl) amino group, N- (dibenzothiophen-3-yl)- N- (2-pyridyl) amino group, N- (dibenzothiophen-3-yl) -N- (2-furyl) amino group, N- (dibenzothiophen-3-yl) -N- (2-thienyl) amino Group, N- (benzo [b] furan-2-yl) -N- (dibenzothiophen-3-yl) amino group, N- (dibenzothiophen-3-yl) -N- (benzo [b] thiophene-2 -Yl) amino group, N- (dibenzothiophen-3-yl) -N- (1-methylindol-2-yl) amino group, N- (dibenzofuran-3-yl) -N- (dibenzothiophene-3- Yl) amino group, N , N-di (2-quinolyl) amino group, N, N-di (4-quinolyl) amino group, N, N-di (5-quinolyl) amino group, N- (2-pyridyl) -N- (2 -Quinolyl) amino group, N- (2-furyl) -N- (2-quinolyl) amino group, N- (2-quinolyl) -N- (2-thienyl) amino group, N- (benzo [b] furan -2-yl) -N- (2-quinolyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-quinolyl) amino group, N- (1-methylindole-2- Yl) -N- (2-quinolyl) amino group, N- (dibenzofuran-3-yl) -N- (2-quinolyl) amino group, N- (dibenzothiophen-3-yl) -N- (2-quinolyl) ) Amino group, N, N-di (1-isoquinolyl) amino group, N- (1-isoquinolyl) N- (2-pyridyl) amino group, N- (2-furyl) -N- (1-isoquinolyl) amino group, N- (1-isoquinolyl) -N- (2-thienyl) amino group, N- (benzo [B] furan-2-yl) -N- (1-isoquinolyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (1-isoquinolyl) amino group, N- (1-isoquinolyl) ) -N- (1-methylindol-2-yl) amino group, N- (dibenzofuran-3-yl) -N- (1-isoquinolyl) amino group, N- (dibenzothiophen-3-yl) -N- (1-isoquinolyl) amino group, N, N-di (2-quinazolinyl) amino group, N, N-di (4-quinazolinyl) amino group, N, N-di (6-quinazolinyl) amino group, N- ( 2-Pyridyl) -N- (2-quinazolini ) Amino group, N- (2-furyl) -N- (2-quinolyl) amino group, N- (2-quinolyl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2 -Yl) -N- (2-quinazolinyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-quinazolinyl) amino group, N- (1-methylindol-2-yl) -N- (2-quinazolinyl) amino group, N- (dibenzofuran-3-yl) -N- (2-quinazolinyl) amino group, N- (dibenzothiophen-3-yl) -N- (2-quinazolinyl) amino Group, N- (2-quinolyl) -N- (2-quinazolinyl) amino group, N, N-di (2-quinoxalinyl) amino group, N, N-di (5-quinoxalinyl) amino group, N, N- Di (6-quinoxalinyl) amino group, N- (2 -Pyridyl) -N- (2-quinoxalinyl) amino group, N- (2-furyl) -N- (2-quinoxalinyl) amino group, N- (2-quinoxalinyl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N- (2-quinoxalinyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-quinoxalinyl) amino group, N- (1-methylindol-2-yl) -N- (2-quinoxalinyl) amino group, N- (dibenzofuran-3-yl) -N- (2-quinoxalinyl) amino group, N- (dibenzothiophen-3-yl) ) -N- (2-quinoxalinyl) amino group, N- (2-quinolyl) -N- (2-quinoxalinyl) amino group, N- (2-quinoxalinyl) -N- (2-quinazolinyl) amino group, N, N-di 9-methylcarbazol-2-yl) amino group, N, N-di (9-methylcarbazol-3-yl) amino group, N- (9-methylcarbazol-2-yl) -N- (2-pyridyl) Amino group, N- (2-furyl) -N- (9-methylcarbazol-2-yl) amino group, N- (9-methylcarbazol-2-yl) -N- (2-thienyl) amino group, N -(Benzo [b] furan-2-yl) -N- (9-methylcarbazol-2-yl) amino group, N- (benzo [b] thiophen-2-yl) -N- (9-methylcarbazole- 2-yl) amino group, N- (1-methylindol-2-yl) -N- (9-methylcarbazol-2-yl) amino group, N- (dibenzofuran-3-yl) -N- (9- Methylcarbazol-2-yl) amino N- (dibenzothiophen-3-yl) -N- (9-methylcarbazol-2-yl) amino group, N- (9-methylcarbazol-2-yl) -N- (2-quinolyl) amino group, N- (1-isoquinolyl) -N- (9-methylcarbazol-2-yl) amino group, N- (9-methylcarbazol-2-yl) -N- (2-quinoxalinyl) amino group, N- (9 -Methylcarbazol-2-yl) -N- (2-quinazolinyl) amino group, N, N-di (3-phenanthridinyl) amino group, N, N-di (4-phenanthridinyl) amino group N, N-di (6-phenanthridinyl) amino group, N- (2-pyridyl) -N- (6-phenanthridinyl) amino group, N- (2-furyl) -N- (6 -Phenanthridinyl) amino group, N- (6-phen Nantridinyl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N- (6-phenanthridinyl) amino group, N- (benzo [b] thiophene-2 -Yl) -N- (6-phenanthridinyl) amino group, N- (1-methylindol-2-yl) -N- (6-phenanthridinyl) amino group, N- (dibenzofuran-3- Yl) -N- (6-phenanthridinyl) amino group, N- (dibenzothiophen-3-yl) -N- (6-phenanthridinyl) amino group, N- (6-phenanthridinyl) -N- (2-quinolyl) amino group, N- (1-isoquinolyl) -N- (6-phenanthridinyl) amino group, N- (6-phenanthridinyl) -N- (2-quinazolinyl) Amino group, N- (6-phenanthridinyl)- -(2-quinoxalinyl) amino group, N- (9-methylcarbazol-2-yl) -N- (6-phenanthridinyl) amino group, N, N-di (2-acridinyl) amino group, N, N-di (3-acridinyl) amino group, N, N-di (9-acridinyl) amino group, N- (9-acridinyl) -N- (2-pyridyl) amino group, N- (9-acridinyl)- N- (2-furyl) amino group, N- (9-acridinyl) -N- (2-thienyl) amino group, N- (9-acridinyl) -N- (benzo [b] furan-2-yl) amino Group, N- (9-acridinyl) -N- (benzo [b] thiophen-2-yl) amino group, N- (9-acridinyl) -N- (1-methylindol-2-yl) amino group, N -(Dibenzofuran-3-yl) -N- ( -Acridinyl) amino group, N- (9-acridinyl) -N- (dibenzothiophen-3-yl) amino group, N- (9-acridinyl) -N- (2-quinolyl) amino group, N- (9- Acridinyl) -N- (1-isoquinolyl) amino group, N- (9-acridinyl) -N- (2-quinazolinyl) amino group, N- (9-acridinyl) -N- (2-quinoxalinyl) amino group, N -(9-acridinyl) -N- (9-methylcarbazol-2-yl) amino group, N- (9-acridinyl) -N- (6-phenanthridinyl) amino group, N, N-di (1 , 10-phenanthrolin-2-yl) amino group, N, N-di (1,10-phenanthroline-3-yl) amino group, N, N-di (1,10-phenanthroline-5-yl) amino group, N- (1 , 10-phenanthrolin-2-yl) -N- (2-pyridyl) amino group, N- (2-furyl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (1,10 -Phenanthrolin-2-yl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (Benzo [b] thiophen-2-yl) -N- (1,10-phenanthroline-2-yl) amino group, N- (1-methylindol-2-yl) -N- (1,10-phenanthroline- 2-yl) amino group, N- (dibenzofuran-3-yl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (dibenzothiophen-3-yl) -N- (1,10 -Phenanthroline-2-y ) Amino group, N- (1,10-phenanthrolin-2-yl) -N- (2-quinolyl) amino group, N- (1-isoquinolyl) -N- (1,10-phenanthrolin-2-yl) amino A group, N- (1,10-phenanthrolin-2-yl) -N- (2-quinazolinyl) amino group, N- (1,10-phenanthrolin-2-yl) -N- (2-quinoxalinyl) amino group, N- (9-methylcarbazol-2-yl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (9-acridinyl) -N- (1,10-phenanthrolin-2-yl) Amino group, N, N-di (1-phenazinyl) amino group, N, N-di (2-phenazinyl) amino group, N- (2-phenazinyl) -N- (2-pyridyl) amino group, N- ( 2-furyl) -N (2-phenazinyl) amino group, N- (2-phenazinyl) -N- (2-thienyl) amino group, N- (benzo [b] furan-2-yl) -N- (2-phenazinyl) amino group, N- (benzo [b] thiophen-2-yl) -N- (2-phenazinyl) amino group, N- (1-methylindol-2-yl) -N- (2-phenazinyl) amino group, N- ( Dibenzofuran-3-yl) -N- (2-phenazinyl) amino group, N- (dibenzothiophen-3-yl) -N- (2-phenazinyl) amino group, N- (2-phenazinyl) -N- (2 -Quinolyl) amino group, N- (1-isoquinolyl) -N- (2-phenazinyl) amino group, N- (2-phenazinyl) -N- (2-quinazolinyl) amino group, N- (2-phenazinyl)- N- (2-Mushroom Salinyl) amino group, N- (9-methylcarbazol-2-yl) -N- (2-phenazinyl) amino group, N- (9-acridinyl) -N- (1-phenazinyl) amino group, N- (9 -Acridinyl) -N- (2-phenazinyl) amino group, N- (2-phenazinyl)
-N- (1,10-phenanthrolin-2-yl) amino group and the like can be mentioned.

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- (2 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 The group N- (benzo [b] furan-2-yl) -N- (3-fluoranthenyl) ami 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-methylindole) -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) Ndol-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- (Diben Zofuran-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, N (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) ) -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) amino 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-naphth Til) 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) amino 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 N- (1-anthryl) -N- (2-quinoxalinyl) amino group, N- (9-phenanthryl) -N- (2-quinoxalinyl) amino group, N- (9,9-dimethylfluoren-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-phenyl) Nantridinyl) -N-pheny Amino 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-phenanthridinyl ) 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-phenanthroline-2-yl) amino group, N- (1-anthryl) -N- (1,10-phenanthroline-2-yl) amino group, N- (1,10-phenanthroline- 2-yl) -N- (9-phenanthryl) amino group, N- (9,9-dimethylfluoren-2-yl) -N- (1,10-phenanthrolin-2-yl) amino group, N- (9 -Fluoranthenyl) -N- (1,10-phenanthroline-2-yl) amino group, N- (3-fluoranthenyl) -N- (1,10-phenanthroline-2-yl) amino group, N-- (1,10-phenanthroline-2-yl) -N- (1-pyrenyl) amino group, N- (1,10-phenanthroline-2-yl) -N- (3-perylenyl) amino group, N-phenyl- N- (2-Fe Dinyl) 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 can be mentioned.

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-phenyl Mino 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) An amino group, N-cyclopentyl-N- (m-tolyl) amino group, -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, -(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-cycl Hexyl-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-ethylamino 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 -Ant ) -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-phenanthryl) ) 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- -Yl) -N-isopropylamino group, N-butyl-N- (9,9-dihexylfluoren-2-yl) amino group, N- (9,9-dimethylfluoren-2-yl) -N-isobutylamino 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-diphenylfluoren-2-yl) -N- Sohexylamino 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-fluorane) Tenenyl) amino group, N- (9-fluoranthenyl) -N-propylamino group, N- (9-fluoranthenyl) -N-isopropylamino group, N-butyl-N- (9-fluoranthenyl) 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-base Zyl-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-Fluorante Nyl) 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-isohexylamino group, N-cyclohexyl-N- (3-fluoranthenyl) amino group, N- Cyclocyclohexylmethyl-N- (3-fluoranthenyl) amino group, N- (3-fluoranthenyl) -N-heptylamino 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, 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-pyrenyl) 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) Mino 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-perylene Nyl) 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-hexyl-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) amino group, N- (4-methoxybenzyl) -N- (3-perylenyl) An amino group, N-furfuryl-N- (3-perylenyl) amino group, etc. are mentioned.

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 group 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 − -(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-isopropylamino 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-furyl) ) Amino group, N- (2-furyl) -N-hexylamino group, N- (2-furyl) -N-isohexylamino group, N-cyclohexyl-N- (2-furyl) amino group, N-cyclohexyl Methyl-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- (2 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 ) -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 ) -N-cyclohexylamino group, N- (benzo [b] furan-2-yl ) -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, -(Benzo [b] thiophen-2-yl) -N-ethylamino group, N- (benzo [b] thiophen-2-yl) -N-propylamino group, N- (benzo [b] thiophen-2-yl 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 ) -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-cyclohexylmethylamino Group, N- (benzo [b] thiophen-2-yl) -N-heptylamino group, N- (benzo [b] thiophen-2-yl) -N-octylamino group, N- (benzo [b] thiophene -2-yl) -N-nonylamino group, N- (benzo [b] thiophen-2-yl) -N-decylamino group, N- (benzo [b] thiophen-2-yl) -N-dodecylamino group, N (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 The group N- (ter -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-mes Tylindol-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- (dibenzothiol) N-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- (dimethyla) Minobenzyl) amino group, N- (dibenzofuran-3-yl) -N- (2-phenethyl) amino group, N- (dibenzofuran-3-yl) -N-furfurylamino group, N- (dibenzothiophen-2-yl) Yl) -N-methylamino group, N- (dibenzothiophen-3-yl)
) -N-methylamino group, N- (dibenzothiophen-3-yl) -N-ethylamino group, N- (dibenzothiophen-3-yl) -N-propylamino group, N- (dibenzothiophen-2-yl) 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- (dibenzothi Phen-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-oct Ruamino 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) a 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- ( -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-N (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 Ru-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-propyl Pil-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- (2 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-methoxy Benzyl) -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-me Tylcarbazol-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- ( -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-dimethylamino) Benzyl) -N- (9-methylcarbazol-2-yl) amino group, N- (4-fluorobenzyl) -N- (9-methylcarbazol-2-yl) amino group, N- (9-methyl) Rucarbazol-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 Mino group, N- (9-acridinyl) -N-hexylamino group, N- (9-acridinyl) -N-isohexylamino 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-me Xylbenzyl) amino group, N- (9-acridinyl) -N- (2-phenethyl) amino group, N- (9-acridinyl) -N-furfurylamino group, N-methyl-N- (1,10-phenanthroline) -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-phenanthrolin-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 substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, An isobutyloxycarbonyl group, a phenoxycarbonyl group, etc. are mentioned.

Specific examples of the compound of the present invention are shown below . Contact name in the table, Ph = Rh = phenyl, o-Tol = ortho - tolyl group, m-Tol = meta - tolyl group, p-Tol = p - tolyl group, 1-Naph = 1-naphthyl, 2- Naph = 2-naphthyl, 1-Anth = 1-anthranyl, 2-Anth = 2-anthranyl, 9-Anth = 9-anthranyl.

（式中、Ｘはハロゲン、その他の基は前記と同一である） The general production method of the present invention is as follows.

(Wherein X is halogen, and other groups are the same as above)

（式中、Ｘはハロゲン、Ｒ ^１ 〜Ｒ ^５ 、Ｒ ^７ 〜Ｒ ^９ 、Ｒ ^１１ は前記と同一であり、Ｒ^２１〜Ｒ^２８はＲ ^４ 、Ｒ ^５ 、Ｒ ^７ 〜Ｒ ^９ 、Ｒ ^１１ のグループと同一のグループから選択される基であるが、ただし、ハロゲン原子を除く）

(In the formula, X is halogen, R ^{1 to} R ⁵ , R ^{7 to} R ⁹ and R ¹¹ are the same as described above, and R ^{21 to} R ²⁸ are R ⁴ , R ⁵ , R ^{7 to} R ⁹ , R ¹¹ . A group selected from the same group as the group, but excluding halogen atoms)

（式中、Ｘはハロゲン、Ｒ ^１ 〜Ｒ ^５ 、Ｒ ^７ 〜Ｒ ^９ 、Ｒ ^１１ は前記と同一であり、Ｒ^３１〜Ｒ^４０はＲ ^４ 〜Ｒ ^５ 、Ｒ ^７ 〜Ｒ ^９ 、Ｒ ^１１ のグループと同一のグループから選択される基であるが、ただし、ハロゲン原子を除く）Ａ

(In the formula, X is halogen, R ^{1 to} R ⁵ , R ^{7 to} R ⁹ , and R ¹¹ are the same as described above, and R ^{31 to} R ⁴⁰ are R ^{4 to} R ⁵ , R ^{7 to} R ⁹ , and R ¹¹ . A group selected from the same group as the group, but excluding a halogen atom)

  These reactions are preferably carried out in an organic solvent, for example, an aromatic solvent such as benzene, toluene, xylene, and ethylbenzene, and the reaction atmosphere is not particularly limited, but an inert atmosphere such as nitrogen, argon, or the like. It is preferable to carry out with. Moreover, it is preferable to perform reaction at 40-150 degreeC, but 100-120 degreeC is especially preferable.

（式中、Ｘはハロゲン、Ｒ ^１ 〜Ｒ ^５ 、Ｒ ^７ 〜Ｒ ^９ 、Ｒ ^１１ 、Ａｒ^１〜Ａｒ^４は前記と同一である） When -N (Ar ¹ , Ar ² ) and -N (Ar ³ , Ar ⁴ ) are not the same, the compound of the present invention is produced, for example, by the following reaction. In the halogenation, it is a matter of course that a necessary part may be blocked to carry out the reaction.

( Wherein X is halogen, R ^{1 to} R ⁵ , R ^{7 to} R ⁹ , R ¹¹ , Ar ^{1 to} Ar ⁴ are the same as above)

  The phenazacillin derivative of the present invention can be used as an organic compound for an organic EL device. In the organic EL device of the present invention, an organic thin film layer composed of a plurality of layers is sandwiched between a cathode and an anode, and the host material of the hole transport layer, hole injection layer or light emitting layer contains a phenazacillin derivative.

  The organic EL device of the present invention is a device in which a multilayer organic thin film layer is laminated between a cathode and an anode as described above. This structure includes (anode / hole transport layer / electron transport layer / light emitting layer / cathode), (anode / hole transport layer / light emitting layer / electron transport layer / cathode), (anode / hole injection layer / hole transport layer / Electron transport layer / light emitting layer / cathode), (Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode), (Anode / hole transport layer / electron transport layer / light emitting layer / electron injection layer / cathode) ), (Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode), (anode / hole injection layer / hole transport layer / electron transport layer / light emitting layer / electron injection layer / cathode), (anode / Hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection 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 / Child transport layer / electron injection layer / cathode), and the like (anode / hole injection layer / hole transport layer / and light emitting layer / electron transport layer / electron injection layer / cathode).

  When the compound of the present invention is used as the host material of the light emitting layer, the light emitting material (doping material) is 1,1,4,4-tetraphenylbutadiene, perylene, 2,5,8,11-tetra-tert- Known fluorescent materials and tris such as butylperylene, coumarin-6, quinacridone, N, N-dimethyl-quinacridone, naphthoquinacridone, tris (8-hydroxyquinolinolato) aluminum, coumarin-C540, coumarin-C545, rubrene, Nile red [2- (2,4-difluorophenyl) pyridine] iridium complex, iridium bis [2- (2,4-difluorophenyl) pyridine] picrate complex, tris (2-phenylpyridine) iridium complex, iridium bis (2-phenyl) Pyridine) acetylacetonate complex, Lis (2-thiophenylpyridine) iridium complex, iridiumbis (2-phenylbenzoxazole) acetylacetonate complex, tris [2- (benzothiophenyl) pyridine] iridium complex, iridiumbis (2-phenylquinoline) acetylacetonate Complex, tris (2-phenylisoquinoline) iridium complex, iridium bis [2- (benzothiophenyl) pyridine] acetylacetonate complex, tris (2-thiophenylisoquinoline) iridium complex, tris [(9,9-dimethyl-2 -Fluorenyl) isoquinoline] iridium complex, 2,3,5,6,8,9,11,12-octaethylporphyrin platinum complex and other known phosphorescent materials can be used in combination. A luminescent material may be used alone or in combination of two or more.

  The organic EL element can prevent a decrease in luminance and lifetime due to quenching by adopting a multilayer structure. Each of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer in the organic EL device of the present invention may be formed of two or more layers. In this case, in the case of a hole injection layer, a layer in which holes are injected from the anode is called a hole injection layer, and a layer that receives holes from the hole injection layer and transports them to the light emitting layer is called a hole transport layer. Similarly, in the case of an electron injection layer, a layer that plays the role of injecting electrons from the cathode is called an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, adhesion with the organic thin film layer or the metal electrode.

  When the compound of the present invention is used as a hole transport layer, one or more hole injection layers can be provided between the anode and the transport layer. As the hole injection material, a material that facilitates the injection of holes from the anode and can smoothly transfer holes injected into the hole transport layer without any obstacles is desirable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, low molecular weight materials such as benzidine type triphenylamines and diamine type triphenylamines, polyaromatic tertiary amine organic Lewis acid doped derivatives, polyethylene dioxythiophene Examples thereof include, but are not limited to, conductive polymer materials such as polystyrene sulfonic acid derivatives, polyaniline polystyrene sulfonic acid derivatives, polyvinyl carbazole derivatives, and polysilane derivatives.

  Of these hole injection layer materials, more effective materials are phthalocyanine derivatives or conductive polymer materials. Each of these has the characteristics of lowering the hole injection barrier from the anode and further improving the smoothness of the film between the anode layer, for example, the indium tin oxide layer and the hole transport layer. Examples of phthalocyanine derivatives include copper phthalocyanine (CuPc), cobalt phthalocyanine (CoPc), nickel phthalocyanine (NiPc), zinc phthalocyanine (ZnPc), palladium phthalocyanine (PdPc), iron phthalocyanine (FePc), manganese phthalocyanine (MnPc), monochloro Examples include, but are not limited to, aluminum phthalocyanine (PcAlCl), monochlorogallium phthalocyanine (PcGaCl), monochloroindium phthalocyanine (PcInCl), and the like. Examples of the conductive polymer material include polyaniline polystyrene sulfonic acid and its sodium salt, polyethylenedioxythiophene polystyrene sulfonic acid and its sodium salt, poly {N- [4- (benzoylphenoxy) phenyl] -N '-( 4-phenoxy) -N, N'-diphenylbenzidine} tri (4-bromophenyl) ammonium pentachloroantimony, but is not limited to these.

  When the compound of the present invention is used as a hole injection layer, it is preferable to provide one or a plurality of hole transport layers between the light emitting layer or the electron transporting and light emitting layer. The material used for the hole transport layer is required to efficiently transport holes injected from the anode or the hole injection layer material to the light emitting layer or the electron transport layer / light emitting layer. Moreover, it is preferable that heat resistance is high and the produced thin film is a thing with high smoothness.

  A typical material used for the hole transport layer is an aromatic tertiary amine. Specific examples thereof include triphenylamine, tridiphenylamine, N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N, N ', N'-(4-Methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N'-diphenyl-N, N'-dinaphthyl-1,1'-biphenyl-4,4 '-Diamine, N, N'-di- (9-phenanthryl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine, N, N, N', N'-tetrabiphenyl -1,1'-biphenyl-4,4'-diamine, 4,4 ', 4 "-tri-[(N-3-methylphenyl) -N-phenyl] -1,1', 1" -triphenyl Amine, 4,4 ', 4 "-tri (N-carbazolyl) -1,1' 1 "-triphenylamine, 4,4 ', 4" -tri-[(N-1-naphthyl) -N-phenyl] -1,1', 1 "-triphenylamine, 4,4'-di- (N, N-di-p-methylphenylanilino) -1,1 ′, 1 ″ -triphenylamine, N, N′-di- [4 ″-(4-N, N′-diphenylanilino) ] -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine, N, N'-di- {4 "-[N, N'-di- (m-methylphenylanilino) -Phenyl]}-N, N'-phenyl-1,1'-biphenyl-4,4'-diamine, N, N'-di- [4- (N-naphthyl-N-phenylanilino) phenyl]- N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine and the like are not limited thereto. Yes.

An electron transport layer and a cathode electrode are necessary for constituting the device. In some cases, an electron injection layer may be provided between the electron transport layer and the cathode.
The material used for the electron transport layer has the ability to transport electrons and has an excellent electron transport effect for the light-emitting layer or light-emitting material, and prevents excitons generated in the light-emitting layer from moving to the hole transport layer. In addition, a compound excellent in thin film formation is desirable.
Further, the electron injection layer needs to have an ability to facilitate the injection of electrons from the cathode and to quickly deliver electrons to the electron transport layer. For this reason, a compound close to the work function of the cathode material is desirable.
Materials used for these include fluorenone, anthraquinodimethane, diphenoquinone, thiopyradixide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and their derivatives. However, it is not limited to these. In the electron injection layer, inorganic compounds such as lithium fluoride, cesium fluoride, and aluminum oxide can also be used.

  In the organic EL device of the present invention, a more effective electron transport material is a metal complex compound, a nitrogen-containing five-membered ring derivative, or a nitrogen-containing aromatic compound. Specific examples of the metal complex compound include tris (8-quinolinato) lithium, tris (8-quinolinato) zinc, tris (8-quinolinato) copper, tris (8-quinolinato) manganese, tris (8-quinolinato) aluminum, tris. (2-Methyl-8-quinolinato) aluminum, tris (4-methyl-8-quinolinato) aluminum, tris (4-propyl-8-quinolinato) aluminum, tris (4-benzyl-8-quinolinato) aluminum, bis (2 -Methyl-8-quinolinato) (phenolate) aluminum, bis (2-methyl-8-quinolinato) (o-cresolate) aluminum, bis (2-methyl-8-quinolinato) (m-cresolate) aluminum, bis (2- Methyl-8-quinolinate) (p- Resoleate) aluminum, bis (2-methyl-8-quinolinato) (m-phenylphenolate) aluminum, bis (2-methyl-8-quinolinato) (p-phenylphenolate) aluminum, bis (2-methyl-8- Quinolinate) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, bis (2 -Methyl-8-quinolinato) (p-cresolate) gallium, bis (8-quinolinato) zinc, bis (8-quinolinato) copper, bis (8-quinolinato) manganese, and the like. Absent.

  Further, specific examples of the nitrogen-containing five-membered ring derivative are preferably an oxazole derivative, a thiazole derivative, an oxadiazole derivative, a thiadiazole derivative, or a triazole derivative. Specifically, 2,5-bis (1-phenyl) -1,3,4-oxazole, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1 -Phenyl) -1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl) )] Benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4'-tert-butylphenyl) -5- (4 "-biphenyl)- 1,3,4-oxadiazole, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-thiazole, 2,5-bis (1-naphthyl)- 1,3,4-thiazole, 1,4-bis [2- (5-phenylthiadi Zolyl)] benzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) -1,3,4 -Triazole, 4-bis [2- (5-phenyltriazolyl)] benzene and the like are exemplified, but not limited thereto.

  Furthermore, a specific example of the nitrogen-containing aromatic compound is preferably a phenanthroline derivative. Specifically, 4,7-diphenyl-1,10-phenanthroline, 4,7-di-m-tolyl-1,10-phenanthroline, 4,7-di-p-tolyl-1,10-phenanthroline, , 9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-di-p-tolyl-1,10-phenanthroline, 2,9-dimethyl-4,7-di -M-tolyl-1,10-phenanthroline, 2,9-diethyl-4,7-diphenyl-1,10-phenanthroline, 2,9-diethyl-4,7-di-p-tolyl-1,10-phenanthroline 2,9-diethyl-4,7-di-m-tolyl-1,10-phenanthroline, 2,9-dimethyl-4,7-bis (naphthalen-1-yl) -1,10-phenanthroline, 2, 9 Dimethyl-4,7-bis (naphthalen-2-yl) -1,10-phenanthroline, 2,9-diphenyl-4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-bis (Biphenylene-4-yl) -1,10-phenanthroline, 3,8-di (α-naphthyl) -1,10-phenanthroline, 3,8-di (β-naphthyl) -1,10-phenanthroline, 1, 4-di (1,10-phenanthrolin-2-yl) benzene, 4,4'-di (1,10-phenanthroline-2-yl) biphenyl, 1,5-di (1,10-phenanthrolin-2-yl) ) Anthracene, 1,3,5-tri (1,10-phenanthrolin-2-yl) benzene and the like, but are not limited thereto.

  As a conductive material used for an anode of an organic electroluminescence element, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium And their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole. As the conductive material used for the cathode, a material having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, and alloys thereof are used. It is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy can be appropriately controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, and the like. The anode and the cathode may be composed of two or more layers as necessary.

  The transparent electrode support substrate used in the organic EL device of the present invention is desirably sufficiently transparent in order to efficiently emit light. The transparent electrode is set using the above-described conductive material so that predetermined translucency can be ensured by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and is transparent, and examples thereof include a glass substrate and a transparent resin film and sheet. Transparent resins used for films and sheets include polyethylene, polyethylene copolymer, polypropylene, polypropylene copolymer, polystyrene, polystyrene copolymer, syndiotactic polystyrene, polymethyl methacrylate, nylon, polyethersulfone, and polysulfone. , Polycarbonate, polycarbonate copolymer, polyarylate, polyetherimide, tetrafluoroethylene-ethylene copolymer, polyvinylidene fluoride, polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and the like.

Formation of each layer of the organic electroluminescence element in the present invention can be performed by a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating or the like.
However, if a conductive polymer is used for the hole injection layer, the hole injection material is laminated by any of the wet film formation methods such as spin coating, dipping, and flow coating before dry film formation, and then heated by vacuum. The solvent must be removed sufficiently by drying.
The thickness of each layer of the organic thin film layer sandwiched between the anode and the cathode is not particularly limited, but must be set to an appropriate thickness. The normal film thickness is preferably selected as appropriate in the range of 0.5 nm to 500 nm.

  In general, when the compound of the present invention is formed into a film, it is desirable to use a vacuum deposition method. However, when used as a hole injection layer, a wet film forming method can be used in addition to the vacuum deposition method. In the wet film forming method, the solvent used for preparing the solution used for forming the organic thin film is dichloromethane, 1,2-dichloroethane, chloroform, tetrahydrofuran, dioxane, 1,2-dimethoxymethane, 1,2-diethoxy. Examples include methane, acetone, and toluene, but are not particularly limited.

  In the organic electroluminescence device of the present invention, in addition to the compound of the present invention, at least one of a hole injection material, a hole transport material, a light emitting material, a doping material, an electron injection material and an electron transport material is contained in the same layer. May be. In addition, in order to improve the stability of the organic electroluminescent device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., it is possible to provide a protective layer on the surface of the device or to protect the entire device with a resin or the like It is.

(1) According to the present invention, a novel phenazacillin derivative could be provided.
(2) By this invention, the compound which can be utilized for an organic EL element was able to be enriched.
(3) According to the present invention, a novel hole transport material, hole injection material, and light emitting layer host material can be provided.
(4) According to the present invention, a novel organic EL device using a new compound can be provided.
(5) The phenazacillin derivative of the present invention is stable for a long time even when used in an organic EL device.

  The present invention will be described below with reference to synthesis examples and examples, but the present invention is not limited thereto.

ジフェニルアミン（１５．０ｇ ８８．６ｍｍｏｌ）を１Ｌ四つ口フラスコに入れ、クロロホルム６００ｍｌに溶解させ、溶液を２℃まで冷却した。Ｎ−ブロモコハク酸イミド（ＮＢＳ）（６６．２ｇ ３７２．１ｍｍｏｌ）を反応液の温度が１０℃を超えないよう３０分かけて徐々に投入した。そのまま５℃で３０分撹拌し、その後室温まで昇温させ、６時間撹拌した。生成物が結晶化し析出していたので反応液を８０℃に加熱し、熱時ろ過を行い、不溶物のコハク酸イミドを除去した。ろ液をロータリーエバポレーターにて濃縮し、茶色粗結晶を得た。この粗結晶を室温にてアセトン３００ｍｌで分散洗浄を２回行い、ろ過した後、６０℃、１２時間真空乾燥してＴＢＤＰＡの薄茶色結晶３０．６ｇを得た。^１Ｈ−ＮＭＲ、元素分析にて構造を確認した。（理論収量４３．０ｇ 収率７１．３％） Synthesis example 1
(Part 1) Synthesis of 2,2 ', 4,4'-tetrabromodiphenylamine (TBDPA)

Diphenylamine (15.0 g 88.6 mmol) was placed in a 1 L four-necked flask and dissolved in 600 ml of chloroform, and the solution was cooled to 2 ° C. N-bromosuccinimide (NBS) (66.2 g 372.1 mmol) was gradually added over 30 minutes so that the temperature of the reaction solution did not exceed 10 ° C. The mixture was stirred as it was at 5 ° C. for 30 minutes, then warmed to room temperature and stirred for 6 hours. Since the product crystallized and precipitated, the reaction solution was heated to 80 ° C. and filtered while hot to remove insoluble succinimide. The filtrate was concentrated with a rotary evaporator to obtain brown crude crystals. The crude crystals were dispersed and washed twice with 300 ml of acetone at room temperature, filtered, and then vacuum dried at 60 ° C. for 12 hours to obtain 30.6 g of light brown crystals of TBDPA. ^The structure was confirmed by ¹ H-NMR and elemental analysis. (Theoretical yield 43.0 g Yield 71.3%)

ＴＢＤＰＡ（３８．９ｇ ８０．２ｍｍｏｌ）とヨードベンゼン（２４．５ｇ １２０．３ｍｍｏｌ）を窒素フローした２００ｍｌ四つ口フラスコに入れ、オルトジクロロベンゼン６０ｍｌに溶解させた。さらに炭酸カリウム（４４．３ｇ ３２０ｍｍｏｌ）、銅粉６０ｇを投入し、１７５℃に加熱しメカニカルスターラーを用いて６５０ｒ．ｐ．ｍ．で２０時間撹拌した。反応終了後、５０℃まで冷却しろ過して銅粉、炭酸カリウムを除去した。ろ液をロータリーエバポレーターで濃縮し、赤茶色粘体を得た。この粘体をｎ−ヘキサン１Ｌに溶解させ、シリカゲルカラムにチャージし、ｎ−ヘキサンで展開して精製した。得られた１スポット溶液をロータリーエバポレーターで濃縮し、無色透明の粘体を得た。この粘体をアセトン３０ｍｌ、メタノール３０ｍｌで再結晶し、６０℃で１２時間真空乾燥してＴＢＮＰＰＡの白色結晶２３．４ｇを得た。^１Ｈ−ＮＭＲ、元素分析にて構造を確認した。（理論収量４５．０ｇ 収率５２．１％） (Part 2) Synthesis of 2,2 ′, 4,4′-tetrabromo-N-phenyl-diphenylamine (TBNPPA)

TBDPA (38.9 g 80.2 mmol) and iodobenzene (24.5 g 120.3 mmol) were placed in a 200 ml four-necked flask with nitrogen flow and dissolved in 60 ml of orthodichlorobenzene. Further, potassium carbonate (44.3 g 320 mmol) and 60 g of copper powder were added, heated to 175 ° C., and 650 r. p. m. For 20 hours. After completion of the reaction, the mixture was cooled to 50 ° C. and filtered to remove copper powder and potassium carbonate. The filtrate was concentrated with a rotary evaporator to obtain a reddish brown viscous body. This viscous body was dissolved in 1 L of n-hexane, charged on a silica gel column, developed with n-hexane and purified. The obtained 1-spot solution was concentrated with a rotary evaporator to obtain a colorless and transparent viscous body. This viscous body was recrystallized with 30 ml of acetone and 30 ml of methanol, and vacuum-dried at 60 ° C. for 12 hours to obtain 23.4 g of TBNPPA white crystals. ^The structure was confirmed by ¹ H-NMR and elemental analysis. (Theoretical yield 45.0g Yield 52.1%)

ＴＢＮＰＰＡ（２０ｇ ３５．７ｍｍｏｌ）をあらかじめ３０分間窒素フローした５００ｍｌ四つ口フラスコに入れ、脱水ジエチルエーテル２５０ｍｌに分散させた。メタノール／氷にて溶液を−１０℃に冷却し、ｎ−ブチルリチウムのヘキサン溶液（使用量４５ｍｌ、溶液濃度１．６Ｍ、使用溶液中のｎ−ブチルリチウムの含有量７１．３ｍｍｏｌ）を１５分かけて滴下した。滴下後反応液を室温まで昇温させ、２時間撹拌した。この溶液をドライアイス、メタノールで−７０℃まで冷却し、ジフェニルジクロロシラン（７．５ｍｌ 比重１．２０４ ９．０ｇ）を５分で滴下した。滴下後、反応液を室温まで昇温させ、１２時間撹拌した。得られた反応液をろ過して不溶物を除去し、ろ液を５％食塩水で２回分液処理した。得られた有機層に硫酸マグネシウム１５ｇを投入し１時間分散してろ過し硫酸マグネシウムを除去した。ろ液をロータリーエバポレーターで濃縮し、薄黄色粗結晶１１．２ｇを得た。この粗結晶をトルエン２５０ｍｌ、ヘキサン２．５Ｌの混合溶媒に５５℃で加熱溶解させ、シリカゲルカラムにチャージし、室温のトルエン／ヘキサン＝１／１０溶液で展開して精製した。得られた１スポット溶液をロータリーエバポレーターで濃縮し、白色結晶を得た。この結晶をアセトン４０ｍｌ／メタノール４０ｍｌ混合溶媒で分散洗浄し、ろ過後、６０℃で１２時間真空乾燥し、ＤＢＮＰＰＨの白色結晶９．０ｇを得た。^１Ｈ−ＮＭＲ、元素分析にて構造を確認した。（理論収量２０．７ｇ 収率４３．６％） (Part 3) Synthesis of 2,8-dibromo-5-phenyl-10,10-diphenyl-5,10-dihydrophenazacillin (DBNPPH)

TBNPPA (20 g 35.7 mmol) was placed in a 500 ml four-necked flask which had been previously nitrogen-flowed for 30 minutes and dispersed in 250 ml of dehydrated diethyl ether. The solution was cooled to −10 ° C. with methanol / ice, and a hexane solution of n-butyllithium (amount used: 45 ml, solution concentration: 1.6 M, content of n-butyllithium in the solution used) was 15 minutes. It was dripped over. After the dropwise addition, the reaction solution was warmed to room temperature and stirred for 2 hours. This solution was cooled to −70 ° C. with dry ice and methanol, and diphenyldichlorosilane (7.5 ml, specific gravity 1.204, 9.0 g) was added dropwise over 5 minutes. After dropping, the reaction solution was warmed to room temperature and stirred for 12 hours. The resulting reaction solution was filtered to remove insoluble matters, and the filtrate was subjected to liquid separation treatment twice with 5% brine. To the obtained organic layer, 15 g of magnesium sulfate was added, dispersed for 1 hour and filtered to remove magnesium sulfate. The filtrate was concentrated with a rotary evaporator to obtain 11.2 g of pale yellow crude crystals. The crude crystals were dissolved by heating in a mixed solvent of 250 ml of toluene and 2.5 L of hexane at 55 ° C., charged on a silica gel column, and purified by developing with a toluene / hexane = 1/10 solution at room temperature. The obtained 1-spot solution was concentrated by a rotary evaporator to obtain white crystals. The crystals were dispersed and washed with a mixed solvent of 40 ml of acetone / 40 ml of methanol, filtered, and vacuum-dried at 60 ° C. for 12 hours to obtain 9.0 g of DBNPPH white crystals. ^The structure was confirmed by ¹ H-NMR and elemental analysis. (Theoretical yield 20.7g Yield 43.6%)

ＤＢＮＰＰＨ（２ｇ ３．４３ｍｍｏｌ）、ジフェニルアミン（１．２２ｇ ７．２０ｍｍｏｌ）、塩化パラジウム（１２．２ｍｇ ０．０６９ｍｍｏｌ） を四つ口フラスコに入れ、オルトキシレン８０ｍｌを投入し、７０℃に加熱して原料を溶解させた。この溶液にトリターシャリーブチルホスフィン（５５．５ｍｇ ０．２７５ｍｍｏｌ）のオルトキシレン１０ｍｌ溶液を加え１４０℃に加熱し３０分撹拌した。塩化パラジウムが溶解しているのを目視で確認後、一旦１２０℃まで冷却し、ナトリウムターシャリーブトキシド（０．９２ｇ ９．６ｍｍｏｌ）をすばやく加え再び１４０℃に加熱し、４時間反応させた。反応終了後、反応液を４０℃まで冷却後ろ過し、ろ液をロータリーエバポレーターで濃縮し薄黄色の粗結晶２．９ｇを得た。この粗結晶をモノクロロベンゼン２００ｍｌ／ヘキサン５００ｍｌの混合溶媒に６０℃で加熱溶解させ、シリカゲルカラムにチャージし、室温のトルエン／ヘキサン１／４溶液で展開して精製した。得られた１スポット溶液をロータリーエバポレーターで濃縮後、濃縮物をアセトン２０ｍｌ／メタノール２０ｍｌ混合溶媒で分散洗浄、ろ過後、６０℃で１２時間真空乾燥してＤＰＮＰＰＨの淡黄色結晶２．２２ｇを得た。^１Ｈ−ＮＭＲ、元素分析にて構造を確認した。（理論収量２．６１ｇ 収率８５．１％） (Part 4) Synthesis of 2,8-di- (diphenylamino) -5-phenyl-10,10-diphenyl-5,10-dihydrophenazacillin (DPNPPH)

DBNPPH (2 g 3.43 mmol), diphenylamine (1.22 g 7.20 mmol), palladium chloride (12.2 mg 0.069 mmol) were placed in a four-necked flask, charged with 80 ml of orthoxylene and heated to 70 ° C. Was dissolved. To this solution, a solution of tritertiary butylphosphine (55.5 mg 0.275 mmol) in orthoxylene 10 ml was added and heated to 140 ° C. and stirred for 30 minutes. After visually confirming that palladium chloride was dissolved, it was once cooled to 120 ° C., sodium tertiary butoxide (0.92 g, 9.6 mmol) was quickly added, and the mixture was heated again to 140 ° C. and reacted for 4 hours. After completion of the reaction, the reaction solution was cooled to 40 ° C. and filtered, and the filtrate was concentrated with a rotary evaporator to obtain 2.9 g of pale yellow crude crystals. The crude crystals were dissolved by heating in a mixed solvent of monochlorobenzene 200 ml / hexane 500 ml at 60 ° C., charged on a silica gel column, developed with a toluene / hexane 1/4 solution at room temperature, and purified. The obtained 1-spot solution was concentrated with a rotary evaporator, and the concentrate was dispersed and washed with a mixed solvent of 20 ml of acetone / 20 ml of methanol, filtered, and then vacuum-dried at 60 ° C. for 12 hours to obtain 2.22 g of DNPPPH pale yellow crystals. . ^The structure was confirmed by ¹ H-NMR and elemental analysis. (Theoretical yield 2.61 g Yield 85.1%)

ジフェニルアミンをｐ，ｐ′−ジトリルアミンとした以外は、仕込み比、反応条件、精製条件等、ＤＰＮＰＰＨ合成と同一の条件で合成した。
（収量２．４４ｇ 理論収量２．８０ｇ 収率８７．２％） Synthesis example 2
Synthesis of 2,8-di- (di-p, p'-tolylamino) -5-phenyl-10,10-diphenyl-5,10-dihydrophenazacillin (DTNPPH)

The synthesis was performed under the same conditions as the DNPPPH synthesis, such as the charging ratio, reaction conditions, and purification conditions, except that diphenylamine was changed to p, p'-ditolylamine.
(Yield 2.44 g Theoretical yield 2.80 g Yield 87.2%)

ジフェニルアミンをカルバゾールとした以外は、仕込み比、反応条件、精製条件等、ＤＰＮＰＰＨ合成と同一の条件で合成した。
（収量２．３２ｇ 理論収量２．５９ｇ 収率８９．６％） Synthesis example 3
Synthesis of 2,8-di- (carbazolyl) -5-phenyl-10,10-diphenyl-5,10-dihydrophenazacillin (CZNPPH)

The synthesis was carried out under the same conditions as the DNPPPH synthesis, such as the charging ratio, reaction conditions, and purification conditions, except that diphenylamine was changed to carbazole.
(Yield 2.32 g Theoretical yield 2.59 g Yield 89.6%)

ＤＢＮＰＰＨを２，８−ジブロモ−５−メチル−１０，１０−ジフェニル−５，１０−ジヒドロフェナザシリン（ＤＢＮＭＰＨ）、ジフェニルアミンをカルバゾールとした以外は、仕込み比、反応条件、精製条件等、ＤＰＮＰＰＨ合成と同一の条件で合成した。
（収量２．３１ｇ 理論収量２．６６ｇ 収率８６．８％） Synthesis example 4
Synthesis of 2,8-di- (carbazolyl) -5-methyl-10,10-diphenyl-5,10-dihydrophenazacillin (CZNMPH)

DNPPPH synthesis except for DBNPPH except for using 2,8-dibromo-5-methyl-10,10-diphenyl-5,10-dihydrophenazacillin (DBNMPH) and diphenylamine as carbazole. Was synthesized under the same conditions.
(Yield 2.31 g Theoretical yield 2.66 g Yield 86.8%)

ＤＢＮＰＰＨをＤＢＮＭＰＨ、ジフェニルアミンをｐ、ｐ′−ジトリルアミンとした以外は、仕込み比、反応条件、精製条件等、ＤＰＮＰＰＨ合成と同一の条件で合成した。
（収量２．４６ｇ 理論収量２．８９ｇ 収率８５．１％） Synthesis example 5
Synthesis of 2,8-di- (p, p'-ditolylamino) -5-methyl-10,10-diphenyl-5,10-dihydrophenazacillin (DTNMPH)

The synthesis was performed under the same conditions as the DNPPPH synthesis except for DBNPPH as DBNMPH and diphenylamine as p and p'-ditolylamine, such as the charging ratio, reaction conditions, and purification conditions.
(Yield 2.46 g Theoretical yield 2.89 g Yield 85.1%)

２，８−ジブロモ−５−フェニル−１０，１０−ジフェニル−５，１０−ジヒドロフェナザシリン（ＤＢＮＰＰＨ）を、２，８−ジブロモ−５−トルイル−１０，１０−ジフェニル−５，１０−ジヒドロフェナザシリン（ＤＢＮＴＰＨ）とした以外は合成例３と同一の条件で合成した。 Synthesis Example 6
Synthesis of 2,8-di- (carbazolyl) -5-toluyl-10,10-diphenyl-5,10-dihydrophenazacillin (CZNTPH)

2,8-Dibromo-5-phenyl-10,10-diphenyl-5,10-dihydrophenazacillin (DBNPPH) was converted to 2,8-dibromo-5-toluyl-10,10-diphenyl-5,10-dihydro. The compound was synthesized under the same conditions as in Synthesis Example 3 except that phenazacillin (DBNTPH) was used.

２，８−ジブロモ−５−フェニル−１０，１０−ジフェニル−５，１０−ジヒドロフェナザシリン（ＤＢＮＰＰＨ）の代わりに２，８−ジブロモ−５−メチル−１０，１０−ジフェニル−５，１０−ジヒドロフェナザシリン（ＤＢＮＭＰＨ）を用いた以外は合成例１のその４と同様にしてＤＰＮＭＰＨを合成した。 Synthesis example 7
Synthesis of 2,8-diphenylamino-5-methyl-10,10-diphenyl-5,10-dihydrophenazacillin (DPNMPH)

2,8-dibromo-5-methyl-10,10-diphenyl-5,10- in place of 2,8-dibromo-5-phenyl-10,10-diphenyl-5,10-dihydrophenazacillin (DBNPPH) DPNMPH was synthesized in the same manner as in Synthesis Example 1, Part 4, except that dihydrophenazacillin (DBNMPH) was used.

  The respective thermal characteristics of CZNPPH of Synthesis Example 3, CZNMPH of Synthesis Example 4, and CZNTPH of Synthesis Example 6 are assumed, and the results are shown below.

なお、表中Ｔｇはガラス転移温度、Ｔｍは融解温度、Ｔｄは熱分解温度を示している。

In the table, Tg represents a glass transition temperature, Tm represents a melting temperature, and Td represents a thermal decomposition temperature.

  In addition, FIG. 3 shows a UV absorption spectrum and FIG. 4 shows a PL spectrum of each deposited film of CZNPPH of Synthesis Example 3, CZNMPH of Synthesis Example 4, CZNTPH of Synthesis Example 6, and DPNMPH of Synthesis Example 7. The UV absorption spectrum and the PL spectrum in the present invention are all measured with a film thickness of 500 mm.

  The electrochemical properties of CZNPPH of Synthesis Example 3, CZNMPH of Synthesis Example 4, CZNTPH of Synthesis Example 6 and DPNMPH of Synthesis Example 7 were measured, and the results are shown in the following table.

なお、表中ＥｇはＵＶ吸収スペクトルの吸収端より算出したエネルギーギャップ値（ＨＯＭＯ値とＬＵＭＯ値の差）、Ｉｐは大気中電子分析にて側定したイオン化ポテンシャル値（ＨＯＭＯ値）、ＥａはＩｐ−Ｅｇにより算出した電子親和力値（エネルギーアフィニティー：ＬＵＭＯ値の差）を示している。

In the table, Eg is an energy gap value (difference between HOMO value and LUMO value) calculated from the absorption edge of the UV absorption spectrum, Ip is an ionization potential value (HOMO value) determined by electron analysis in air, and Ea is Ip -Shows the electron affinity value (energy affinity: difference in LUMO value) calculated by Eg.

From the above data, among the compounds of the present invention, those having a carbazole group showed a considerably high value of Tg of about 170 to 186 ° C. It is the highest level among Tg of currently reported low molecular weight compounds. Planarity is lost due to the influence of the phenyl group bonded to silicon of the central phenazacillin skeleton and bulky carbazole, and the crystallinity is considered to be lowered. Therefore, high film forming properties can be expected. There is almost no shift of the UV spectrum and PL spectrum due to the substituent of the N atom at the center of the phenazacillin derivative having a carbazole group, and these substituents (phenyl group, tolyl group) are considered to contribute little to the conjugated structure. . In other words, it may be twisted and bound to the phenazacillin plane.
The Eg estimated from the UV absorption edge of the phenazacillin derivative having a carbazole group is about 3.3 eV, which is a wider gap than the DPNMPH of Synthesis Example 7 which is a phenazacillin derivative of the present invention having no α-NPD or carbazole group. It was. The peak of the PL spectrum is observed in the vicinity of 400 nm for all the compounds, and blue shifts from DPNMPH (430 nm), which is the phenazacillin derivative of the present invention having no carbazole group in Synthesis Example 7, but is described later in Comparative Example 2 described later. It is red-shifted from DTASI (375 nm) shown in FIG. There is concern about how much the triplet level will drop. Moreover, Ip is about 5.7 to 5.8 eV, which is measured by AC-1 [trade name of oxidation potential measuring instrument manufactured by Riken Keiki Co., Ltd.] and shows a large value as a hole transport material. In this case, it is predicted that high voltage driving is performed.

  The thermal characteristics of DPNMPH of Synthesis Example 7, DNPPPH of Synthesis Example 1, DTNMPH of Synthesis Example 5, and DTNPPH of Synthesis Example 2 were measured, and the results are shown below.

  Further, for each of the deposited films of DPNMPH of Synthesis Example 7, DNPPPH of Synthesis Example 1, DTNMPH of Synthesis Example 5, DTNPPH of Synthesis Example 2, and CZNMPH of Synthesis Example 4, FIG. 5 shows the UV absorption spectrum and FIG. It is shown in FIG.

  Electrochemistry of DPNMPH of Synthesis Example 7, DNPPPH of Synthesis Example 1, DTNMPH of Synthesis Example 5, DTNPPH of Synthesis Example 2, and CZNMPH of Synthesis Example 4 of the present invention having α-NPD and carbazole group for comparison The characteristics are shown in the table below.

  The Tg of the PH derivative of the present invention having a diphenylamino group instead of a carbazole group, such as DPNMPH in Synthesis Example 7, DNPPPH in Synthesis Example 1, DTNMPH in Synthesis Example 5, and DTNPPH in Synthesis Example 2, is 100 ° C. or more. And not as good as the CZPH derivative. The crystallization temperature was observed when DNPPPH of Synthesis Example 1 and DTNPPH of Synthesis Example 2 which are N-phenyl-substituted products were further raised from the glass transition temperature. Since the melting points of these two compounds are higher than the melting points of DPNMPH in Synthesis Example 7 and DTNMPH in Synthesis Example 5 of the N-methyl substituted product, it is considered that the crystallinity is relatively high. Further, like the CZPH derivative, there is almost no shift in UV and PL spectra due to the substituent of the N atom, and it is considered that the N-phenyl group hardly contributes to the conjugated structure. The Eg of the PH derivative is about 2.9 to 3.0 eV, unfortunately not a wide gap. However, any compound has an Ip lower than that of α-NPD, and when applied to a device, a high hole injection property can be expected.

耐久寿命試験のための測定条件：１０ｍＡ／ｃｍ^２定電流駆動
初期輝度：ＤＰＡＳＩ、ＤＴＡＳＩ、α−ＮＰＤの場合、約５００ｃｄ／ｍ^２、
ＤＰＮＭＰＨの場合、約１５０ｃｄ／ｍ^２
相対輝度変化、電圧変化をそれぞれ図１および２に示す。また輝度半減時間を下記表６５にまとめた。 Example 1, Comparative Examples 1-3
(1) Device configuration ITO / MCC-PB-162 (200Å) / hole transport layer (300Å) / Alq (600Å) / LiF (5Å) / Al (1000Å)
The hole transport layer is
Comparative Example 1: DPASI 500 cd / m ²
Comparative Example 2: DTASI 500 cd / m ²
Comparative Example 3: α-NPD 500 cd / m ²
Example 1: DPNMPH (Synthesis Example 7) 150 cd / m ²
It was.
MCC-PB-162: a hole injection agent (trade name) manufactured by Mitsubishi Chemical Corporation, and the chemical structural formula of DPASI, DTASI, α-NPD, DPNMPH, Alq [Tris (8-quinolinolato) aluminum] is as follows. It is as follows.

Measurement conditions for endurance life test: 10 mA / cm ² Constant current drive initial luminance: In the case of DPASI, DTASI, α-NPD, about 500 cd / m ² ,
In the case of DPNMPH, about 150 cd / m ²
The relative luminance change and the voltage change are shown in FIGS. 1 and 2, respectively. The luminance half time is summarized in Table 65 below.

Since DPNMPH has a half-life of luminance that is too long, it has not reached half-life at the report creation stage, and at this pace, the half-life is estimated to be about 4000 hours. At first glance, DPNMPH seems to have a very good endurance life, but since the initial luminance is only about 1/3 that of an element using α-NPD, it cannot be simply compared. Assuming that the initial luminance and the half-time are inversely proportional, the half-time of the element using the DNPMPH (Example 1) is estimated to be about 1200 hr at the initial luminance of 500 cd / m ² and is almost equivalent to α-NPD. I can say that. The reason why the initial luminance of DPNMPH is low is considered that holes are difficult to be injected into the Alq layer because the HOMO level is 5.30 eV, which is higher than α-NPD. For this reason, it is considered that holes are accumulated excessively near the DPNMPH / Alq interface. Although it is a hypothesis, even if such a phenomenon is taken into consideration, since it shows almost the same durability as α-NPD, it can be assumed that the stability of the cation radical of DPNMPH is high.
Further, DTASI (Comparative Example 2) and DPASI (Comparative Example 1) having the same tetraphenylsilane skeleton have extremely poor durability life. Since the durability of DPNMPH in which the same silicon atom is introduced is not bad, it is not likely to be simply the influence of the silicon atom. The cause is not clear, but it may be due to chemical stability.

Examples 2 to 5 (the compound of the present invention was used for the hole transport layer and Alq was used for the light emitting layer), Comparative Examples 4 and 5
(1) Device configuration:
(Part 1) In an ITO / CZPH derivative (500Å) / Alq (600Å) / LiF (5Å) / Al (1000Å) element,
Example 2: Using CZNMPH of Synthesis Example 4 as CZPH derivative Example 3: Using CZNPPH of Synthesis Example 3 as CZPH derivative Comparative example 4: Using α-NPD instead of CZPH derivative (Part 2) ITO / TPDPES: In a TBPAH (10 wt% 200 Å) / CZPH derivative (300 Å) / Alq (600 Å) / LiF (5 Å) / Al (1000 Å) device,
Example 4: Use CZNMPH of Synthesis Example 4 as CZPH derivative Example 5: Use CZNPPH of Synthesis Example 3 as CZPH derivative Comparative Example 5: Use α-NPD instead of CZPH derivative (2) Device performance An organic EL element is manufactured, and voltage-current characteristics and voltage-luminance characteristics are shown in FIGS. The EL spectrum is shown in FIG. These device characteristics are shown in the following table.

＠は印加電圧を示す。

@ Indicates the applied voltage.

All the devices of Examples 2 to 5 and Comparative Examples 4 to 5 emitted Alq-derived light having a peak near 530 nm. When the EL element using CZNMPH (Ip 5.79 eV) of Example 2 is compared with Example 3 CZNPPH (5.73 eV), the element of Example 3 using CZNPPH is slightly driven at a lower voltage. However, as predicted from Ip, both of them were driven at a higher voltage than the element of Comparative Example 4 using α-NPD. It seems that holes are much less likely to be injected from ITO. In the EL elements of Examples 4 and 5 and Comparative Example 5 using TPDPES: TBPAH, the above tendency was improved.

ＦＩｒｐｉｃ{ビス〔２−（４，６−ジフルオロフェニル）ピリジナト〕ピコリナトイリジウム（III）}

ＢＡｌｑ：Ｂｉｓ（２−Ｍｅｔｙｌ−８−ｈｙｄｒｏｘｙｑｕｉｎｏｌｉｎｏｌａｔｏ）（４−ｐｈｅｎｙｌｐｈｅｎｏｘｙ）Ａｌｕｍｉｎｕｍ
（２）素子の性能
これらの素子のＥＬスペクトルを図１２に、電圧−電流特性を図１３に、電圧−輝度特性を図１４に、電圧−視感効率特性は図１５に、電圧−電流効率特性は図１６に、それぞれ示すと共に、各素子の特性を下記表に示す。 Examples 6-7, Comparative Example 6
(1) Device configuration: (blue phosphorescent device):
ITO / TPDPES: TBPAH (10 wt% 200 Å) / hole transport layer (300 Å) / CBP: FIrpic (8 wt% 300 Ｂ) / BAlq (300 Å) / LiF (5 Å) / Al (1000 Å)
When α-NPD is used for the hole transport layer (Comparative Example 6)
When CZNMPH of Synthesis Example 4 is used for the hole transport layer (Example 6)
When CZNPPH of Synthesis Example 3 is used for the hole transport layer (Example 7)
CBP [4,4'-dicarbazolylbiphenyl]

FIrpic {Bis [2- (4,6-difluorophenyl) pyridinato] picorinatoiridium (III)}

BAlq: Bis (2-Methyl-8-hydroxyquinolinolato) (4-phenylphenoxy) Aluminum
(2) Device Performance The EL spectrum of these devices is shown in FIG. 12, the voltage-current characteristics in FIG. 13, the voltage-luminance characteristics in FIG. 14, the voltage-luminous efficiency characteristics in FIG. The characteristics are shown in FIG. 16 and the characteristics of each element are shown in the following table.

＠は印加電圧を示す。

@ Indicates the applied voltage.

  Light emission from only FIrpic having a peak in the vicinity of 470 nm is observed from any element, and it seems that no leakage of electrons to the hole transport layer occurs when the doping concentration is around 8 wt%. Comparing the maximum external quantum efficiency, CZNPPH and CZNMPH are both about 11% compared to 3.20% of α-NPD, and it is considered that the wide gap property of these CZPH derivatives contributed to higher efficiency.

Examples 8-11, Comparative Example 7
(1) Device configuration: (two-layer device with Alq):
ITO / hole transport layer (500 mm) / Alq (600 mm) / LiF (5 mm) / Al (1000 mm)
When α-NPD is used for the hole transport layer (Comparative Example 7)
When DPNMPH of Synthesis Example 7 is used for the hole transport layer (Example 8)
When DNPPPH of Synthesis Example 1 is used for the hole transport layer (Example 9)
When DTNMPH of Synthesis Example 5 is used for the hole transport layer (Example 10)
When DTNPPH of Synthesis Example 2 is used for the hole transport layer (Example 11)
(2) Device performance FIG. 7 shows the EL spectrum of these devices, FIG. 18 shows the voltage-current characteristics, FIG. 19 shows the voltage-luminance characteristics, and the characteristics of each device are shown in the following table.

＠は印加電圧を示す。

@ Indicates the applied voltage.

  All of the devices using the PH derivative of the present invention of the type having a diphenylamino group had a lower luminance than a device using α-NPD, although a larger current density was observed. As a reason for this, since the Ip of the PH derivative is lower than α-NPD, hole injection from ITO is easy, but it is considered that hole injection from the PH derivative to Alq is difficult. In addition, the EL spectrum has a red shift of about 15 to 20 nm as compared with the element using α-NPD, suggesting some interaction such as exciplex formation between the PH derivative and Alq. This may also be a cause of reduced efficiency. For these reasons, PH derivatives are more suitable for hole injection materials than hole transport materials.

Examples 12-15, Comparative Example 8
(1) Device configuration: (PH derivative as hole injection material):
ITO / hole injection layer (200Å) / α-NPD (300Å) / Alq (600Å) / LiF (5Å) / Al (1000Å)
When DPNMPH of Synthesis Example 7 is used for the hole injection layer (Example 12)
When DNPPPH of Synthesis Example 1 is used for the hole injection layer (Example 13)
When DTNMPH of Synthesis Example 5 is used for the hole injection layer (Example 14)
When DTNPPH of Synthesis Example 2 is used for the hole injection layer (Example 15)
TPDPES: TBPAH (10wt%) for hole injection layer
(Comparative Example 8)
(2) Device performance The EL spectrum of these devices is shown in FIG. 20, the voltage-current characteristics are shown in FIG. 21, the voltage-luminance characteristics are shown in FIG. 22, and the characteristics of each device are shown in the following table.

＠は印加電圧を示す。

@ Indicates the applied voltage.

（２）素子の性能
これらの素子の電圧−電流特性を図２３に、電圧−輝度特性を図２４に、電圧−視感効率特性を図２５に、電圧−電流効率特性を図２６に、それぞれ示すと共に、各素子の特性を下記表に示す。 Examples 16-17, Comparative Example 9
(1) Device configuration: (CZPH derivative as host material)
ITO / TPDPES: TBPAH (10 wt% 200 Å) / 2-NPD (300 ／) / the following CZPH derivative (9 wt%) dopedIr (ppy) ₃ ^{* (1)} (300 Å) / BCP (100 Å) / Alq ₃ (200 Å) / LiF (5cm) / Al (1000mm)
Example 16: Use CZNMPH of Synthesis Example 4 as CZPH derivative Example 17: Use CZNTPH of Synthesis Example 6 as CZPH derivative Comparative Example 9: Use CBP (Chemical Formula 18) instead of CZPH derivative
^{* (1)} Ir (ppy) ₃ [Tris (2-phenylpyridinato) iridium (III)]

(2) Device performance FIG. 23 shows the voltage-current characteristics of these devices, FIG. 24 shows the voltage-luminance characteristics, FIG. 25 shows the voltage-luminous efficiency characteristics, and FIG. 26 shows the voltage-current efficiency characteristics. The characteristics of each element are shown in the following table.

ＣＺＮＭＰＨ、ＣＺＮＴＰＨを用いた素子は、最大外部量子効率が１０％を超えており、Ｉｒ（ｐｐｙ）_３の三重項励起子の閉じこめ効果があると考えられる。

A device using CZNMPH or CZNTPH has a maximum external quantum efficiency exceeding 10%, and is considered to have a confinement effect of triplet excitons of Ir (ppy) ₃ .

Alq emission having a peak in the vicinity of about 530 nm was observed although there was a slight shift from any device using the PH derivative as the hole injection layer. From the voltage-current characteristics and voltage luminance characteristics, these elements are both more than α-NPD single elements [ITO // α-NPD (300 Å) / Alq (600 Å) / LiF (5 Å) / Al (1000 Å)]. Obviously, the result of driving at a low voltage is obtained. It can be said that the hole injection barrier from ITO is relaxed by the low Ip of the PH derivative.
Comparing the current densities at 5 V of the four types of PH derivatives, the current of DTNPPH (Example 15) with the lowest Ip is the lowest, and it seems that the current does not tend to easily enter as Ip is lower. The mobility in the amorphous state of the material also seems to be related. Comparing the current injection properties of the device using TPDPES: TBPAH doped with Lewis acid (Comparative Example 8) and the device using Examples (Examples 12 to 15), there is no significant difference in the region of high voltage (6 V or more). However, in the low voltage region of 6 V or less, Comparative Example 8 (TPDPES: TBPAH) tends to be slightly better. While it is a comparative example 8 (TPDPES: TBPAH) spin coat film, the PH derivative is a vapor deposition film, and the influence of the roughness of ITO may be reflected.
The PH derivative has a higher Tg than the starburst amine known so far as a low-molecular hole injection material, and does not contaminate the chamber like copper phthalocyanine. Useful as.

It is a graph which shows the relative luminance change of DPASI used in the comparative example 1, DTASI used in the comparative example 2, (alpha) -NPD used in the comparative example 3, and DPNMPH used in Example 1. FIG. It is a graph which shows the voltage change of DPASI used in the comparative example 1, DTASI used in the comparative example 2, (alpha) -NPD used in the comparative example 3, and DPNMPH used in Example 1. FIG. The UV absorption spectrum of each vapor deposition film | membrane of CZNPPH of the synthesis example 3, CZNMPH of the synthesis example 4, CZNTPH of the synthesis example 6, and DPNMPH of the synthesis example 7 is shown. The PL spectra of the deposited films of CZNPPH of Synthesis Example 3, CZNMPH of Synthesis Example 4, CZNTPH of Synthesis Example 6, and DPNMPH of Synthesis Example 7 are shown. The UV absorption spectrum of each vapor deposition film | membrane of DNPPPH of the synthesis example 1, DTNPPH of the synthesis example 2, DTNMPH of the synthesis example 5, DPNMPH of the synthesis example 7, and CZNMPH of the synthesis example 4 is shown. The PL spectra of the respective deposited films of DNPPPH of Synthesis Example 1, DTNPPH of Synthesis Example 2, DTNMPH of Synthesis Example 5, DPNMPH of Synthesis Example 7, and CZNMPH of Synthesis Example 4 are shown. The voltage-current characteristics of the device using α-NPD of Comparative Example 4, the device using CZNMPH of Example 2, and the device using CZNPPH of Example 3 are shown. The voltage-luminance characteristics of the device using α-NPD of Comparative Example 4, the device using CZNMPH of Example 2, and the device using CZNPPH of Example 3 are shown. TPDPES of Comparative Example 5: device using TBPAH / α-NPD, TPDPES of Example 4: TBPAH / device using CZNMPH of Synthesis Example 4, TPDPES of Example 5: TBPAH / device of Synthesis Example 3 CZNPPH The voltage-current characteristic is shown. TPDPES of Comparative Example 5: device using TBPAH / α-NPD, TPDPES of Example 4: TBPAH / device using CZNMPH of Synthesis Example 4, TPDPES of Example 5: TBPAH / device of Synthesis Example 3 CZNPPH Voltage-luminance characteristics are shown. The EL spectrum in 25 mA / cm < ² > of each vapor deposition film of (alpha) -NPD of the comparative example 5, CZNMPH of Example 4, and CZNPPH of Example 5 is shown. The EL spectrum in 25 mA / cm < ² > of each vapor deposition film of (alpha) -NPD of the comparative example 6, CZNMPH of Example 6, and CZNPPH of Example 7 is shown. The voltage-current characteristics of the device using α-NPD of Comparative Example 6, the device using CZNMPH of Example 6, and the device using CZNPPH of Example 7 are shown. The voltage-current characteristics of the device using α-NPD of Comparative Example 6, the device using CZNMPH of Example 6, and the device using CZNPPH of Example 7 are shown. The voltage-luminous efficiency characteristic of the element using (alpha) -NPD of the comparative example 6, the element using CZNMPH of Example 6, and the element using CZNPPH of Example 7 is shown. The voltage-current efficiency characteristic of the element using (alpha) -NPD of the comparative example 6, the element using CZNMPH of Example 6, and the element using CZNPPH of Example 7 is shown. Vapor deposition film using α-NPD of Comparative Example 7, Vapor deposition film using DPNMPH of Example 8, Vapor deposition film using DNPPPH of Example 9, Vapor deposition film using DPNMPH of Example 10, DPNPPH shows the EL spectra of each of 25mA / cm ² of deposited film was used. Vapor deposition film using α-NPD of Comparative Example 7, Vapor deposition film using DPNMPH of Example 8, Vapor deposition film using DNPPPH of Example 9, Vapor deposition film using DPNMPH of Example 10, Each voltage-current characteristic of the vapor deposition film using DNPPPH is shown. Vapor deposition film using α-NPD of Comparative Example 7, Vapor deposition film using DPNMPH of Example 8, Vapor deposition film using DNPPPH of Example 9, Vapor deposition film using DPNMPH of Example 10, Each voltage-luminance characteristic of the vapor deposition film using DPPMPH is shown. The EL spectra at 25 mA / cm ² for α-NPD alone, DPNMPH of Synthesis Example 7, DNPPPH of Synthesis Example 1, DTMPH of Synthesis Example 5, and DTNPPH of Synthesis Example 2 are shown. TPDPES in Comparative Example 8: An element using TBPAH, an element using DPNMP in Example 12, an element using DNPPH in Example 13, and an element using DTMPH in Example 14 of Example 15. Each voltage-current characteristic of the element using DTNPPH is shown. TPDPES in Comparative Example 8: An element using TBPAH, an element using DPNMP in Example 12, an element using DNPPH in Example 13, and an element using DTMPH in Example 14 of Example 15. Each voltage-luminance characteristic of the element using DTNPPH is shown. The voltage-current characteristics of the element using CZNTPH of Example 17 and the element using CBP of Comparative Example 9 of the element using CZNMPH of Example 16 are shown. The voltage-luminance characteristics of the device using CZNMPH of Example 16 and the device using CZNTPH of Example 17 and the device using CBP of Comparative Example 9 are shown. The voltage-luminous efficiency characteristics of the element using CZNTPH of Example 17 and the element using CBP of Comparative Example 9 of the element using CZNMPH of Example 16 are shown. The voltage-current efficiency characteristic of the element using CBP of the comparative example 9 of the element using CZNTPH of Example 17 of the element using CZNMPH of Example 16 is shown.

Claims (7)

A phenazacillin derivative represented by the following general formula (1) .

Wherein, R ¹ is a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group or al election Barre groups consisting of group, R ^2, R ³ is a substituted or unsubstituted aryl group R ⁴ , R ⁵ , R ^{7 to} R ⁹ and R ¹¹ are a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a perfluoroalkyl having 1 to 20 carbon atoms. Group, substituted or unsubstituted alkenyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 45 carbon atoms, substituted or unsubstituted heteroaryl group having 4 to 40 carbon atoms, 3 to 40 carbon atoms Organic silicon group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted arylsulfonyl group having 6 to 20 carbon atoms, substituted Or Substituted dialkylamino group having 2 to 30 carbon atoms, substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, substituted or unsubstituted diheteroarylamino group having 8 to 40 carbon atoms, substituted or unsubstituted carbon A 10 to 40 arylheteroarylamino group, a substituted or unsubstituted alkylarylamino group having 7 to 40 carbon atoms, a substituted or unsubstituted alkylheteroarylamino group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon R ⁶ is a group independently selected from the group consisting of alkoxycarbonyl groups of 2 to 30, R ⁶ is —N (Ar ¹ , Ar ² ), and R ¹⁰ is —N (Ar ¹ , Ar a ²⁾ or ^{-N (Ar 3, Ar 4)} . Ar ^{1 to} Ar ⁴ are substituted or unsubstituted aryl groups, and Ar ¹ and Ar ² , and / or Ar ³ and Ar ⁴ are combined to form a substituted or unsubstituted heterocyclic ring, respectively. It may be formed. In addition, the substituent in the “substitution” is an alkyl group having 1 to 4 carbon atoms. ]   A hole transport material comprising the phenazacillin derivative according to claim 1.   A hole injection material comprising the phenazacillin derivative according to claim 1.   A light emitting layer host material comprising the phenazacillin derivative according to claim 1.   An organic EL device comprising the phenazacillin derivative according to claim 1.   An organic EL device, wherein the phenazacillin derivative according to claim 1 is used in at least one layer selected from the group consisting of a hole transport layer, a hole injection layer, and a light emitting layer.   The organic EL device according to claim 6, wherein a phosphorescent material is used as the light emitting material.

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