JP2007063478A - Polyaminopyridine and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide polyaminopyridines having highly efficient light-emitting performances and a method for producing them. <P>SOLUTION: The polyaminopyridines have a recurring unit expressed by general formula (1) [wherein, R<SP>1</SP>is H, a 1-10C alkyl, an alkoxy, an alkanoyl, carbamoyl or cyano; and R<SP>2</SP>is a fused polycyclic carbon ring group which may have a substituent, a single ring type heterocyclic ring group which may have a substituent or a fused polycyclic heterocyclic ring group which may have a substituent], and have average molecular weights in the range of 500-1,000,000, and the method for producing them is also provided. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to polyaminopyridines and a method for producing the same. More specifically, the present invention relates to polyaminopyridines having a high-efficiency light-emitting function used for polymer-type organic electroluminescence (hereinafter abbreviated as EL) materials and the production method thereof.

  Polyaminopyridines are used for conductive functions such as capacitors, antistatic agents, IC boards, electron beam IC circuit patterning, applications using oxidation / reduction functions such as batteries and electroluminescence elements, transistors, diodes, solar cells, etc. In addition to applications utilizing the electronic device functions, photoconductive materials, advanced optical communication elements (nonlinear optical elements), applications utilizing optical functions such as optical computers, etc., they are used in electromagnetic shielding materials, plastic magnets, and the like.

  As such polyaminopyridines, for example, polyaminopyridines obtained by oxidative polymerization of aminopyridines are known (see Patent Document 1).

However, polyaminopyridines obtained by oxidative polymerization of aminopyridine are polymers in which the pyridine ring is bonded at various positions, and are partially branched or cross-linked, so they have low solubility in various solvents. , Its use is severely limited.
Therefore, as a result of studies to improve the solubility in such a solvent, it was found that specific polyaminopyridines have a good solubility in a solvent, and the present applicant has developed a polymer-type organic electroluminescent material. Patent applications have already been filed for such polyaminopyridines used (see Patent Document 2).
JP-A-61-85440 International Publication No. 2005/030838 Pamphlet

  Applications of polymer organic electroluminescent materials are diversified today, and various polyaminopyridines having a high-efficiency light-emitting function are required in order to respond to such applications.

  While the present inventors have investigated the aminopyridines in this patent by changing the side chain substituents, polyaminopyridine having various substituents completely different from the substituents in Patent Document 2 emits light with high efficiency. It has been found that it has a function, and the present invention has been completed.

The present invention relates to polyaminopyridines and methods for producing the same as shown below.
Item 1. General formula (1):

Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkanoyl group, a carbamoyl group or a cyano group, and R ² is a condensed polycyclic carbocyclic group which may have a substituent. Represents a monocyclic heterocyclic group which may have a substituent or a condensed polycyclic heterocyclic group which may have a substituent.), And has a number average molecular weight of 500 Polyaminopyridines in the range of ~ 1000000.

Item 2. Item 2. The polyaminopyridine according to Item 1, wherein, in the general formula (1), R ¹ is a hydrogen atom, and R ² is a perylenyl group, an acridinyl group, or a coumarinyl group.

  Item 3. General formula (2):

(Wherein R ¹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkanoyl group, a carbamoyl group or a cyano group, and X represents a halogen atom) Pyridines and general formula (3):

Wherein R ² is a condensed polycyclic carbocyclic group which may have a substituent, a monocyclic heterocyclic group which may have a substituent, or a condensed polycyclic which may have a substituent. And a compound represented by the general formula (1), wherein the amine compound represented by formula (1) is reacted in the presence of a base with a palladium compound and a phosphine compound as catalysts.

(Wherein, ^{R 1} is the same as ^{R 1} in the general formula (2), ^{R 2} is the same as ^{R 2} is in the formula (3).) Has a repeating unit represented by the number A method for producing polyaminopyridines having an average molecular weight in the range of 500 to 1,000,000.

Hereinafter, the present invention will be described in detail.
The polyaminopyridines of the present invention are compounds having a repeating unit represented by the following general formula (1) and having a number average molecular weight in the range of 500 to 1,000,000.

In the general formula (1), R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkanoyl group, a carbamoyl group, or a cyano group, and R ² is a condensed polycyclic ring that may have a substituent. It represents a carbocyclic group, a monocyclic heterocyclic group which may have a substituent or a condensed polycyclic heterocyclic group which may have a substituent.

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ¹ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n -Pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl group, n-octyl group, n-decyl group and the like.
Examples of the alkoxy group include a methoxy group and an ethoxy group.
Examples of the alkanoyl group include a methanoyl group and an ethanoyl group.

The condensed polycyclic carbocyclic group that may have a substituent represented by R ² includes a naphthyl group that may have a substituent, an anthryl group that may have a substituent, and a substituent. Excluding a pyrenyl group which may have, for example, a pentarenyl group which may have a substituent, an indenyl group which may have a substituent, an azulenyl group which may have a substituent, a substitution A heptalenyl group which may have a group, an acenaphthyl group which may have a substituent, a fluorenyl group which may have a substituent, a phenalenyl group which may have a substituent, and a substituent A good phenanthryl group, a fluoranthenyl group that may have a substituent, a triphenylenyl group that may have a substituent, a perylenyl group that may have a substituent, a chrysenyl group that may have a substituent, Optionally substituted picenyl group, substituted Examples thereof include a pentacenyl group which may have a group, a coronyl group which may have a substituent, and an oberenyl group which may have a substituent.

  Examples of the monocyclic heterocyclic group that may have a substituent are those that exclude a pyridyl group that may have a substituent and a pyrimidyl group that may have a substituent. Furyl group which may have, thiophenyl group which may have substituent, thiopyrenyl group which may have substituent, pyrazinyl group which may have substituent and pyridazinyl which may have substituent Groups and the like.

  The condensed polycyclic heterocyclic group which may have a substituent is a group other than the quinolyl group which may have a substituent, for example, a benzofuryl group which may have a substituent, a substituent An isobenzofuryl group which may have a substituent, a 1-benzothiophenyl group which may have a substituent, a 2-benzothiophenyl group which may have a substituent, a carbazoyl which may have a substituent Group, an optionally substituted xanthenyl group, an optionally substituted isoquinolyl group, an optionally substituted acridinyl group, an optionally substituted quinoxalyl group, and a substituent. And a coumarinyl group which may be used.

Among these represented as R ² , from the viewpoint of obtaining high luminous efficiency, a perylenyl group which may have a substituent, an acridinyl group which may have a substituent, and a coumarinyl which may have a substituent Groups are preferably used.

  Specific examples of the perylenyl group which may have a substituent include 1-perylenyl group, 2-perylenyl group, 3-perylenyl group, 2-methyl-1-perylenyl group, 2-ethyl-1-perylenyl group, 2 -N-hexyl-1-perylenyl group, 2-n-octyl-1-perylenyl group, 2-n-decyl-1-perylenyl group, 3-methyl-1-perylenyl group, 3-ethyl-1-perylenyl group, 3-n-hexyl-1-perylenyl group, 3-n-octyl-1-perylenyl group, 3-n-decyl-1-perylenyl group, 4-methyl-1-perylenyl group, 4-ethyl-1-perylenyl group 4-n-hexyl-1-perylenyl group, 4-n-octyl-1-perylenyl group, 4-n-decyl-1-perylenyl group, 5-methyl-1-perylenyl group, 5-ethyl-1-perylenyl Group, 5- -Hexyl-1-perylenyl group, 5-n-octyl-1-perylenyl group, 5-n-decyl-1-perylenyl group, 6-methyl-1-perylenyl group, 6-ethyl-1-perylenyl group, 6- n-hexyl-1-perylenyl group, 6-n-octyl-1-perylenyl group, 6-n-decyl-1-perylenyl group, 7-methyl-1-perylenyl group, 7-ethyl-1-perylenyl group, 7 -N-hexyl-1-perylenyl group, 7-n-octyl-1-perylenyl group, 7-n-decyl-1-perylenyl group, 8-methyl-1-perylenyl group, 8-ethyl-1-perylenyl group, 8-n-hexyl-1-perylenyl group, 8-n-octyl-1-perylenyl group, 8-n-decyl-1-perylenyl group, 9-methyl-1-perylenyl group, 9-ethyl-1-perylenyl group , 9-n Hexyl-1-perylenyl group, 9-n-octyl-1-perylenyl group, 9-n-decyl-1-perylenyl group, 10-methyl-1-perylenyl group, 10-ethyl-1-perylenyl group, 10-n -Hexyl-1-perylenyl group, 10-n-octyl-1-perylenyl group, 10-n-decyl-1-perylenyl group, 11-methyl-1-perylenyl group, 11-ethyl-1-perylenyl group, 11- n-hexyl-1-perylenyl group, 11-n-octyl-1-perylenyl group, 11-n-decyl-1-perylenyl group, 12-methyl-1-perylenyl group, 12-ethyl-1-perylenyl group, 12 -N-hexyl-1-perylenyl group, 12-n-octyl-1-perylenyl group, 12-n-decyl-1-perylenyl group, 1-methyl-2-perylenyl group, 1-ethyl 2-perylenyl group, 1-n-hexyl-2-perylenyl group, 1-n-octyl-2-perylenyl group, 1-n-decyl-2-perylenyl group, 3-methyl-2-perylenyl group, 3- Ethyl-2-perylenyl group, 3-n-hexyl-2-perylenyl group, 3-n-octyl-2-perylenyl group, 3-n-decyl-2-perylenyl group, 4-methyl-2-perylenyl group, 4 -Ethyl-2-perylenyl group, 4-n-hexyl-2-perylenyl group, 4-n-octyl-2-perylenyl group, 4-n-decyl-2-perylenyl group, 5-methyl-2-perylenyl group, 5-ethyl-2-perylenyl group, 5-n-hexyl-2-perylenyl group, 5-n-octyl-2-perylenyl group, 5-n-decyl-2-perylenyl group, 6-methyl-2-perylenyl group 6-ethyl- -Perylenyl group, 6-n-hexyl-2-perylenyl group, 6-n-octyl-2-perylenyl group, 6-n-decyl-2-perylenyl group, 7-methyl-2-perylenyl group, 7-ethyl- 2-perylenyl group, 7-n-hexyl-2-perylenyl group, 7-n-octyl-2-perylenyl group, 7-n-decyl-2-perylenyl group, 8-methyl-2-perylenyl group, 8-ethyl 2-perylenyl group, 8-n-hexyl-2-perylenyl group, 8-n-octyl-2-perylenyl group, 8-n-decyl-2-perylenyl group, 9-methyl-2-perylenyl group, 9- Ethyl-2-perylenyl group, 9-n-hexyl-2-perylenyl group, 9-n-octyl-2-perylenyl group, 9-n-decyl-2-perylenyl group, 10-methyl-2-perylenyl group, 10 -Ethyl 2-perylenyl group, 10-n-hexyl-2-perylenyl group, 10-n-octyl-2-perylenyl group, 10-n-decyl-2-perylenyl group, 11-methyl-2-perylenyl group, 11-ethyl 2-perylenyl group, 11-n-hexyl-2-perylenyl group, 11-n-octyl-2-perylenyl group, 11-n-decyl-2-perylenyl group, 12-methyl-2-perylenyl group, 12- Ethyl-2-perylenyl group, 12-n-hexyl-2-perylenyl group, 12-n-octyl-2-perylenyl group, 12-n-decyl-2-perylenyl group, 1-methyl-3-perylenyl group, 1 -Ethyl-3-perenyl group, 1-n-hexyl-3-perylenyl group, 1-n-octyl-3-perylenyl group, 1-n-decyl-3-perylenyl group, 2-methyl-3-pe Lylenyl group, 2-ethyl-3-perylenyl group, 2-n-hexyl-3-perylenyl group, 2-n-octyl-3-perylenyl group, 2-n-decyl-3-perylenyl group, 4-methyl-3 -Perylenyl group, 4-ethyl-3-perylenyl group, 4-n-hexyl-3-perylenyl group, 4-n-octyl-3-perylenyl group, 4-n-decyl-3-perylenyl group, 5-methyl- 3-perylenyl group, 5-ethyl-3-perylenyl group, 5-n-hexyl-3-perylenyl group, 5-n-octyl-3-perylenyl group, 5-n-decyl-3-perylenyl group, 6-methyl -3-perylenyl group, 6-ethyl-3-perylenyl group, 6-n-hexyl-3-perylenyl group, 6-n-octyl-3-perylenyl group, 6-n-decyl-3-perylenyl group, 7- Methyl-3-peri Nyl group, 7-ethyl-3-perylenyl group, 7-n-hexyl-3-perylenyl group, 7-n-octyl-3-perylenyl group, 7-n-decyl-3-perylenyl group, 8-methyl-3 -Perylenyl group, 8-ethyl-3-perylenyl group, 8-n-hexyl-3-perylenyl group, 8-n-octyl-3-perylenyl group, 8-n-decyl-3-perylenyl group, 9-methyl- 3-perylenyl group, 9-ethyl-3-perylenyl group, 9-n-hexyl-3-perylenyl group, 9-n-octyl-3-perylenyl group, 9-n-decyl-3-perylenyl group, 10-methyl -3-perylenyl group, 10-ethyl-3-perylenyl group, 10-n-hexyl-3-perylenyl group, 10-n-octyl-3-perylenyl group, 10-n-decyl-3-perylenyl group, 11- Methyl 3-perylenyl group, 11-ethyl-3-perylenyl group, 11-n-hexyl-3-perylenyl group, 11-n-octyl-3-perylenyl group, 11-n-decyl-3-perylenyl group, 12-methyl -3-perylenyl group, 12-ethyl-3-perylenyl group, 12-n-hexyl-3-perylenyl group, 12-n-octyl-3-perylenyl group, 12-n-decyl-3-perylenyl group, 2- Methoxy-1-perylenyl group, 2-methanoyl-1-perylenyl group, 2-carbamoyl-1-perylenyl group, 2-cyano-1-perylenyl group, 1-methoxy-2-perylenyl group, 1-methanoyl-2-perylenyl Group, 1-carbamoyl-2-perylenyl group, 1-cyano-2-perylenyl group and the like.

Specific examples of the acridinyl group which may have a substituent include 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 2-methyl-1-acridinyl group, 2-ethyl-1-acridinyl group, 2-n-hexyl-1-acridinyl group, 2-n-octyl-1-acridinyl group, 2-n-decyl-1-acridinyl group, 3-methyl-1-acridinyl group 3-ethyl-1-acridinyl group, 3-n-hexyl-1-acridinyl group, 3-n-octyl-1-acridinyl group, 3-n-decyl-1-acridinyl group, 4-methyl-1-acridinyl Group, 4-ethyl-1-acridinyl group, 4-n-hexyl-1-acridinyl group, 4-n-octyl-1-acridinyl group, 4-n-decyl-1-a Lydinyl group, 5-methyl-1-acridinyl group, 5-ethyl-1-acridinyl group, 5-n-hexyl-1-acridinyl group, 5-n-octyl-1-acridinyl group, 5-n-decyl-1 -Acridinyl group, 6-methyl-1-acridinyl group, 6-ethyl-1-acridinyl group, 6-n-hexyl-1-acridinyl group, 6-n-octyl-1-acridinyl group, 6-n-decyl- 1-acridinyl group, 7-methyl-1-acridinyl group, 7-ethyl-1-acridinyl group, 7-n-hexyl-1-acridinyl group, 7-n-octyl-1-acridinyl group, 7-n-decyl -1-acridinyl group, 8-methyl-1-acridinyl group, 8-ethyl-1-acridinyl group, 8-n-hexyl-1-acridinyl group, 8-n-octyl-1- Cridinyl group, 8-n-decyl-1-acridinyl group, 9-methyl-1-acridinyl group, 9-ethyl-1-acridinyl group, 9-n-hexyl-1-acridinyl group, 9-n-octyl-1 -Acridinyl group, 9-n-decyl-1-acridinyl group, 1-methyl-2-acridinyl group, 1-ethyl-2-acridinyl group, 1-n-hexyl-2-acridinyl group, 1-n-octyl- 2-acridinyl group, 1-n-decyl-2-acridinyl group, 3-methyl-2-acridinyl group, 3-ethyl-2-acridinyl group, 3-n-hexyl-2-acridinyl group, 3-n-octyl 2-acridinyl group, 3-n-decyl-2-acridinyl group, 4-methyl-2-acridinyl group, 4-ethyl-2-acridinyl group, 4-n-hexyl-2-a Cridinyl group, 4-n-octyl-2-acridinyl group, 4-n-decyl-2-acridinyl group, 5-methyl-2-acridinyl group, 5-ethyl-2-acridinyl group, 5-n-hexyl-2 -Acridinyl group, 5-n-octyl-2-acridinyl group, 5-n-decyl-2-acridinyl group, 6-methyl-2-acridinyl group, 6-ethyl-2-acridinyl group, 6-n-hexyl- 2-acridinyl group, 6-n-octyl-2-acridinyl group, 6-n-decyl-2-acridinyl group, 7-methyl-2-acridinyl group, 7-ethyl-2-acridinyl group, 7-n-hexyl 2-acridinyl group, 7-n-octyl-2-acridinyl group, 7-n-decyl-2-acridinyl group, 8-methyl-2-acridinyl group, 8-ethyl-2-a Lydinyl group, 8-n-hexyl-2-acridinyl group, 8-n-octyl-2-acridinyl group, 8-n-decyl-2-acridinyl group, 9-methyl-2-acridinyl group, 9-ethyl-2 -Acridinyl group, 9-n-hexyl-2-acridinyl group, 9-n-octyl-2-acridinyl group, 9-n-decyl-2-acridinyl group, 1-methyl-3-acridinyl group, 1-ethyl- 3-acridinyl group, 1-n-hexyl-3-acridinyl group, 1-n-octyl-3-acridinyl group, 1-n-decyl-3-acridinyl group, 2-methyl-3-acridinyl group, 2-ethyl -3-acridinyl group, 2-n-hexyl-3-acridinyl group, 2-n-octyl-3-acridinyl group, 2-n-decyl-3-acridinyl group, 4-methyl- -Acridinyl group, 4-ethyl-3-acridinyl group, 4-n-hexyl-3-acridinyl group, 4-n-octyl-3-acridinyl group, 4-n-decyl-3-acridinyl group, 5-methyl- 3-acridinyl group, 5-ethyl-3-acridinyl group, 5-n-hexyl-3-acridinyl group, 5-n-octyl-3-acridinyl group, 5-n-decyl-3-acridinyl group, 6-methyl -3-acridinyl group, 6-ethyl-3-acridinyl group, 6-n-hexyl-3-acridinyl group, 6-n-octyl-3-acridinyl group, 6-n-decyl-3-acridinyl group, 7- Methyl-3-acridinyl group, 7-ethyl-3-acridinyl group, 7-n-hexyl-3-acridinyl group, 7-n-octyl-3-acridinyl group, 7-n-decyl Ru-3-acridinyl group, 8-methyl-3-acridinyl group, 8-ethyl-3-acridinyl group, 8-n-hexyl-3-acridinyl group, 8-n-octyl-3-acridinyl group, 8-n -Decyl-3-acridinyl group, 9-methyl-3-acridinyl group, 9-ethyl-3-acridinyl group, 9-n-hexyl-3-acridinyl group, 9-n-octyl-3-acridinyl group, 9- n-decyl-3-acridinyl group, 1-methyl-4-acridinyl group, 1-ethyl-4-acridinyl group, 1-n-hexyl-4-acridinyl group, 1-n-octyl-4-acridinyl group, 1 -N-decyl-4-acridinyl group, 2-methyl-4-acridinyl group, 2-ethyl-4-acridinyl group, 2-n-hexyl-4-acridinyl group, 2-n-octyl Ru-4-acridinyl group, 2-n-decyl-4-acridinyl group, 3-methyl-4-acridinyl group, 3-ethyl-4-acridinyl group, 3-n-hexyl-4-acridinyl group, 3-n -Octyl-4-acridinyl group, 3-n-decyl-4-acridinyl group, 5-methyl-4-acridinyl group, 5-ethyl-4-acridinyl group, 5-n-hexyl-4-acridinyl group, 5- n-octyl-4-acridinyl group, 5-n-decyl-4-acridinyl group, 6-methyl-4-acridinyl group, 6-ethyl-4-acridinyl group, 6-n-hexyl-4-acridinyl group, 6 -N-octyl-4-acridinyl group, 6-n-decyl-4-acridinyl group, 7-methyl-4-acridinyl group, 7-ethyl-4-acridinyl group, 7-n-hex Ru-4-acridinyl group, 7-n-octyl-4-acridinyl group, 7-n-decyl-4-acridinyl group, 8-methyl-4-acridinyl group, 8-ethyl-4-acridinyl group, 8-n -Hexyl-4-acridinyl group, 8-n-octyl-4-acridinyl group, 8-n-decyl-4-acridinyl group, 9-methyl-4-acridinyl group, 9-ethyl-4-acridinyl group, 9- n-hexyl-4-acridinyl group, 9-n-octyl-4-acridinyl group, 9-n-decyl-4-acridinyl group, 1-methyl-5-acridinyl group, 1-ethyl-5-acridinyl group, 1 -N-hexyl-5-acridinyl group, 1-n-octyl-5-acridinyl group, 1-n-decyl-5-acridinyl group, 2-methyl-5-acridinyl group, 2-ethy Ru-5-acridinyl group, 2-n-hexyl-5-acridinyl group, 2-n-octyl-5-acridinyl group, 2-n-decyl-5-acridinyl group, 3-methyl-5-acridinyl group, 3 -Ethyl-5-acridinyl group, 3-n-hexyl-5-acridinyl group, 3-n-octyl-5-acridinyl group, 3-n-decyl-5-acridinyl group, 4-methyl-5-acridinyl group, 4-ethyl-5-acridinyl group, 4-n-hexyl-5-acridinyl group, 4-n-octyl-5-acridinyl group, 4-n-decyl-5-acridinyl group, 6-methyl-5-acridinyl group 6-ethyl-5-acridinyl group, 6-n-hexyl-5-acridinyl group, 6-n-octyl-5-acridinyl group, 6-n-decyl-5-acridinyl group, 7 Methyl-5-acridinyl group, 7-ethyl-5-acridinyl group, 7-n-hexyl-5-acridinyl group, 7-n-octyl-5-acridinyl group, 7-n-decyl-5-acridinyl group, 8 -Methyl-5-acridinyl group, 8-ethyl-5-acridinyl group, 8-n-hexyl-5-acridinyl group, 8-n-octyl-5-acridinyl group, 8-n-decyl-5-acridinyl group, 9-methyl-5-acridinyl group, 9-ethyl-5-acridinyl group, 9-n-hexyl-5-acridinyl group, 9-n-octyl-5-acridinyl group, 9-n-decyl-5-acridinyl group 1-methyl-6-acridinyl group, 1-ethyl-6-acridinyl group, 1-n-hexyl-6-acridinyl group, 1-n-octyl-6-acridinyl group, -N-decyl-6-acridinyl group, 2-methyl-6-acridinyl group, 2-ethyl-6-acridinyl group, 2-n-hexyl-6-acridinyl group, 2-n-octyl-6-acridinyl group, 2-n-decyl-6-acridinyl group, 3-methyl-6-acridinyl group, 3-ethyl-6-acridinyl group, 3-n-hexyl-6-acridinyl group, 3-n-octyl-6-acridinyl group 3-n-decyl-6-acridinyl group, 4-methyl-6-acridinyl group, 4-ethyl-6-acridinyl group, 4-n-hexyl-6-acridinyl group, 4-n-octyl-6-acridinyl Group, 4-n-decyl-6-acridinyl group, 5-methyl-6-acridinyl group, 5-ethyl-6-acridinyl group, 5-n-hexyl-6-acridinyl group, 5 -N-octyl-6-acridinyl group, 5-n-decyl-6-acridinyl group, 7-methyl-6-acridinyl group, 7-ethyl-6-acridinyl group, 7-n-hexyl-6-acridinyl group, 7-n-octyl-6-acridinyl group, 7-n-decyl-6-acridinyl group, 8-methyl-6-acridinyl group, 8-ethyl-6-acridinyl group, 8-n-hexyl-6-acridinyl group 8-n-octyl-6-acridinyl group, 8-n-decyl-6-acridinyl group, 9-methyl-6-acridinyl group, 9-ethyl-6-acridinyl group, 9-n-hexyl-6-acridinyl Group, 9-n-octyl-6-acridinyl group, 9-n-decyl-6-acridinyl group, 1-methyl-7-acridinyl group, 1-ethyl-7-acridinyl group, 1 n-hexyl-7-acridinyl group, 1-n-octyl-7-acridinyl group, 1-n-decyl-7-acridinyl group, 2-methyl-7-acridinyl group, 2-ethyl-7-acridinyl group, 2 -N-hexyl-7-acridinyl group, 2-n-octyl-7-acridinyl group, 2-n-decyl-7-acridinyl group, 3-methyl-7-acridinyl group, 3-ethyl-7-acridinyl group, 3-n-hexyl-7-acridinyl group, 3-n-octyl-7-acridinyl group, 3-n-decyl-7-acridinyl group, 4-methyl-7-acridinyl group, 4-ethyl-7-acridinyl group 4-n-hexyl-7-acridinyl group, 4-n-octyl-7-acridinyl group, 4-n-decyl-7-acridinyl group, 5-methyl-7-acridinyl group 5-ethyl-7-acridinyl group, 5-n-hexyl-7-acridinyl group, 5-n-octyl-7-acridinyl group, 5-n-decyl-7-acridinyl group, 6-methyl-7-acridinyl Group, 6-ethyl-7-acridinyl group, 6-n-hexyl-7-acridinyl group, 6-n-octyl-7-acridinyl group, 6-n-decyl-7-acridinyl group, 8-methyl-7- Acridinyl group, 8-ethyl-7-acridinyl group, 8-n-hexyl-7-acridinyl group, 8-n-octyl-7-acridinyl group, 8-n-decyl-7-acridinyl group, 9-methyl-7 -Acridinyl group, 9-ethyl-7-acridinyl group, 9-n-hexyl-7-acridinyl group, 9-n-octyl-7-acridinyl group, 9-n-decyl-7-acridin Nyl group, 1-methyl-8-acridinyl group, 1-ethyl-8-acridinyl group, 1-n-hexyl-8-acridinyl group, 1-n-octyl-8-acridinyl group, 1-n-decyl-8 -Acridinyl group, 2-methyl-8-acridinyl group, 2-ethyl-8-acridinyl group, 2-n-hexyl-8-acridinyl group, 2-n-octyl-8-acridinyl group, 2-n-decyl- 8-acridinyl group, 3-methyl-8-acridinyl group, 3-ethyl-8-acridinyl group, 3-n-hexyl-8-acridinyl group, 3-n-octyl-8-acridinyl group, 3-n-decyl -8-acridinyl group, 4-methyl-8-acridinyl group, 4-ethyl-8-acridinyl group, 4-n-hexyl-8-acridinyl group, 4-n-octyl-8-acrylic group Nyl group, 4-n-decyl-8-acridinyl group, 5-methyl-8-acridinyl group, 5-ethyl-8-acridinyl group, 5-n-hexyl-8-acridinyl group, 5-n-octyl-8 -Acridinyl group, 5-n-decyl-8-acridinyl group, 6-methyl-8-acridinyl group, 6-ethyl-8-acridinyl group, 6-n-hexyl-8-acridinyl group, 6-n-octyl- 8-acridinyl group, 6-n-decyl-8-acridinyl group, 7-methyl-8-acridinyl group, 7-ethyl-8-acridinyl group, 7-n-hexyl-8-acridinyl group, 7-n-octyl -8-acridinyl group, 7-n-decyl-8-acridinyl group, 9-methyl-8-acridinyl group, 9-ethyl-8-acridinyl group, 9-n-hexyl-8-acrylic Nyl group, 9-n-octyl-8-acridinyl group, 9-n-decyl-8-acridinyl group, 1-methyl-9-acridinyl group, 1-ethyl-9-acridinyl group, 1-n-hexyl-9 -Acridinyl group, 1-n-octyl-9-acridinyl group, 1-n-decyl-9-acridinyl group, 2-methyl-9-acridinyl group, 2-ethyl-9-acridinyl group, 2-n-hexyl- 9-acridinyl group, 2-n-octyl-9-acridinyl group, 2-n-decyl-9-acridinyl group, 3-methyl-9-acridinyl group, 3-ethyl-9-acridinyl group, 3-n-hexyl -9-acridinyl group, 3-n-octyl-9-acridinyl group, 3-n-decyl-9-acridinyl group, 4-methyl-9-acridinyl group, 4-ethyl-9-acridin Nyl group, 4-n-hexyl-9-acridinyl group, 4-n-octyl-9-acridinyl group, 4-n-decyl-9-acridinyl group, 5-methyl-9-acridinyl group, 5-ethyl-9 -Acridinyl group, 5-n-hexyl-9-acridinyl group, 5-n-octyl-9-acridinyl group, 5-n-decyl-9-acridinyl group, 6-methyl-9-acridinyl group, 6-ethyl- 9-acridinyl group, 6-n-hexyl-9-acridinyl group, 6-n-octyl-9-acridinyl group, 6-n-decyl-9-acridinyl group, 7-methyl-9-acridinyl group, 7-ethyl -9-acridinyl group, 7-n-hexyl-9-acridinyl group, 7-n-octyl-9-acridinyl group, 7-n-decyl-9-acridinyl group, 8-methyl-9-a Lydinyl group, 8-ethyl-9-acridinyl group, 8-n-hexyl-9-acridinyl group, 8-n-octyl-9-acridinyl group, 8-n-decyl-9-acridinyl group, 2-methoxy-1 -Acridinyl group, 2-methanoyl-1-acridinyl group, 2-carbamoyl-1-acridinyl group, 2-cyano-1-acridinyl group, 1-methoxy-2-acridinyl group, 1-methanoyl-2-acridinyl group, 1 -Carbamoyl-2-acridinyl group, 1-cyano-2-acridinyl group, etc. are mentioned.

  Specific examples of the coumarinyl group which may have a substituent include 3-coumarinyl group, 4-coumarinyl group, 5-coumarinyl group, 6-coumarinyl group, 7-coumarinyl group, 8-coumarinyl group, 4-methyl- 3-coumarinyl group, 4-ethyl-3-coumarinyl group, 4-n-hexyl-3-coumarinyl group, 4-n-octyl-3-coumarinyl group, 4-n-decyl-3-coumarinyl group, 5-methyl -3-coumarinyl group, 5-ethyl-3-coumarinyl group, 5-n-hexyl-3-coumarinyl group, 5-n-octyl-3-coumarinyl group, 5-n-decyl-3-coumarinyl group, 6- Methyl-3-coumarinyl group, 6-ethyl-3-coumarinyl group, 6-n-hexyl-3-coumarinyl group, 6-n-octyl-3-coumarinyl group, 6-n-decyl-3-coumarinyl group, 7 -Methyl 3-coumarinyl group, 7-ethyl-3-coumarinyl group, 7-n-hexyl-3-coumarinyl group, 7-n-octyl-3-coumarinyl group, 7-n-decyl-3-coumarinyl group, 8-methyl -3-coumarinyl group, 8-ethyl-3-coumarinyl group, 8-n-hexyl-3-coumarinyl group, 8-n-octyl-3-coumarinyl group, 8-n-decyl-3-coumarinyl group, 3- Methyl-4-coumarinyl group, 3-ethyl-4-coumarinyl group, 3-n-hexyl-4-coumarinyl group, 3-n-octyl-4-coumarinyl group, 3-n-decyl-4-coumarinyl group, 5 -Methyl-4-coumarinyl group, 5-ethyl-4-coumarinyl group, 5-n-hexyl-4-coumarinyl group, 5-n-octyl-4-coumarinyl group, 5-n-decyl-4-coumarinyl group, 6-methyl- -Coumarinyl group, 6-ethyl-4-coumarinyl group, 6-n-hexyl-4-coumarinyl group, 6-n-octyl-4-coumarinyl group, 6-n-decyl-4-coumarinyl group, 7-methyl- 4-coumarinyl group, 7-ethyl-4-coumarinyl group, 7-n-hexyl-4-coumarinyl group, 7-n-octyl-4-coumarinyl group, 7-n-decyl-4-coumarinyl group, 8-methyl -4-coumarinyl group, 8-ethyl-4-coumarinyl group, 8-n-hexyl-4-coumarinyl group, 8-n-octyl-4-coumarinyl group, 8-n-decyl-4-coumarinyl group, 3- Methyl-5-coumarinyl group, 3-ethyl-5-coumarinyl group, 3-n-hexyl-5-coumarinyl group, 3-n-octyl-5-coumarinyl group, 3-n-decyl-5-coumarinyl group, 4 -Methyl-5 Coumarinyl group, 4-ethyl-5-coumarinyl group, 4-n-hexyl-5-coumarinyl group, 4-n-octyl-5-coumarinyl group, 4-n-decyl-5-coumarinyl group, 6-methyl-5 -Coumarinyl group, 6-ethyl-5-coumarinyl group, 6-n-hexyl-5-coumarinyl group, 6-n-octyl-5-coumarinyl group, 6-n-decyl-5-coumarinyl group, 7-methyl- 5-coumarinyl group, 7-ethyl-5-coumarinyl group, 7-n-hexyl-5-coumarinyl group, 7-n-octyl-5-coumarinyl group, 7-n-decyl-5-coumarinyl group, 8-methyl -5-coumarinyl group, 8-ethyl-5-coumarinyl group, 8-n-hexyl-5-coumarinyl group, 8-n-octyl-5-coumarinyl group, 8-n-decyl-5-coumarinyl group, 3- Methyl-6- Linyl group, 3-ethyl-6-coumarinyl group, 3-n-hexyl-6-coumarinyl group, 3-n-octyl-6-coumarinyl group, 3-n-decyl-6-coumarinyl group, 4-methyl-6 -Coumarinyl group, 4-ethyl-6-coumarinyl group, 4-n-hexyl-6-coumarinyl group, 4-n-octyl-6-coumarinyl group, 4-n-decyl-6-coumarinyl group, 5-methyl- 6-coumarinyl group, 5-ethyl-6-coumarinyl group, 5-n-hexyl-6-coumarinyl group, 5-n-octyl-6-coumarinyl group, 5-n-decyl-6-coumarinyl group, 7-methyl -6-coumarinyl group, 7-ethyl-6-coumarinyl group, 7-n-hexyl-6-coumarinyl group, 7-n-octyl-6-coumarinyl group, 7-n-decyl-6-coumarinyl group, 8- Methyl-6-bear Nyl group, 8-ethyl-6-coumarinyl group, 8-n-hexyl-6-coumarinyl group, 8-n-octyl-6-coumarinyl group, 8-n-decyl-6-coumarinyl group, 3-methyl-7 -Coumarinyl group, 3-ethyl-7-coumarinyl group, 3-n-hexyl-7-coumarinyl group, 3-n-octyl-7-coumarinyl group, 3-n-decyl-7-coumarinyl group, 4-methyl- 7-coumarinyl group, 4-ethyl-7-coumarinyl group, 4-n-hexyl-7-coumarinyl group, 4-n-octyl-7-coumarinyl group, 4-n-decyl-7-coumarinyl group, 5-methyl -7-coumarinyl group, 5-ethyl-7-coumarinyl group, 5-n-hexyl-7-coumarinyl group, 5-n-octyl-7-coumarinyl group, 5-n-decyl-7-coumarinyl group, 6- Methyl-7-coumalini Group, 6-ethyl-7-coumarinyl group, 6-n-hexyl-7-coumarinyl group, 6-n-octyl-7-coumarinyl group, 6-n-decyl-7-coumarinyl group, 8-methyl-7 -Coumarinyl group, 8-ethyl-7-coumarinyl group, 8-n-hexyl-7-coumarinyl group, 8-n-octyl-7-coumarinyl group, 8-n-decyl-7-coumarinyl group, 3-methyl- 8-coumarinyl group, 3-ethyl-8-coumarinyl group, 3-n-hexyl-8-coumarinyl group, 3-n-octyl-8-coumarinyl group, 3-n-decyl-8-coumarinyl group, 4-methyl -8-coumarinyl group, 4-ethyl-8-coumarinyl group, 4-n-hexyl-8-coumarinyl group, 4-n-octyl-8-coumarinyl group, 4-n-decyl-8-coumarinyl group, 5- Methyl-8-coumarinyl 5-ethyl-8-coumarinyl group, 5-n-hexyl-8-coumarinyl group, 5-n-octyl-8-coumarinyl group, 5-n-decyl-8-coumarinyl group, 6-methyl-8-coumarinyl Group, 6-ethyl-8-coumarinyl group, 6-n-hexyl-8-coumarinyl group, 6-n-octyl-8-coumarinyl group, 6-n-decyl-8-coumarinyl group, 7-methyl-8- Coumarinyl group, 7-ethyl-8-coumarinyl group, 7-n-hexyl-8-coumarinyl group, 7-n-octyl-8-coumarinyl group, 7-n-decyl-8-coumarinyl group, 3-methyl-8 -Coumarinyl group, 3-ethyl-8-coumarinyl group, 3-n-hexyl-8-coumarinyl group, 3-n-octyl-8-coumarinyl group, 3-n-decyl-8-coumarinyl group, 4-methyl- 8-coumarinyl group 4-ethyl-8-coumarinyl group, 4-n-hexyl-8-coumarinyl group, 4-n-octyl-8-coumarinyl group, 4-n-decyl-8-coumarinyl group, 5-methyl-8-coumarinyl group 5-ethyl-8-coumarinyl group, 5-n-hexyl-8-coumarinyl group, 5-n-octyl-8-coumarinyl group, 5-n-decyl-8-coumarinyl group, 6-methyl-8-coumarinyl Group, 6-ethyl-8-coumarinyl group, 6-n-hexyl-8-coumarinyl group, 6-n-octyl-8-coumarinyl group, 6-n-decyl-8-coumarinyl group, 7-methyl-8- Coumarinyl group, 7-ethyl-8-coumarinyl group, 7-n-hexyl-8-coumarinyl group, 7-n-octyl-8-coumarinyl group, 7-n-decyl-8-coumarinyl group, 4-methoxy-3 -Coumarinyl group, 4-methanoyl-3-coumarinyl group, 4-carbamoyl-3-coumarinyl group, 4-cyano-3-coumarinyl group, 3-methoxy-4-coumarinyl group, 3-methanoyl-4-coumarinyl group, 3-carbamoyl-4 -Coumarinyl group, 3-cyano-4-coumarinyl group and the like.

  Among these, since they are easily available, the perylenyl group of 1-perylenyl group, 2-perylenyl group and 3-perylenyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group and An acridinyl group of 9-acridinyl group and a coumarinyl group of 3-coumarinyl group, 4-coumarinyl group, 5-coumarinyl group, 6-coumarinyl group, 7-coumarinyl group and 8-coumarinyl group are more preferably used.

  Specific examples of the polyaminopyridines of the present invention include poly (2- (N-1-perylenyl) aminopyridine), poly (2- (N-2-perylenyl) aminopyridine), poly (2- (N-3) -Perylenyl) aminopyridine), poly (2- (N-5-methyl-2-perylenyl) aminopyridine), poly (2- (N-5-ethyl-2-perylenyl) aminopyridine), poly (2- ( N-5-n-hexyl-2-perylenyl) aminopyridine), poly (2- (N-5-n-octyl-2-perylenyl) aminopyridine), poly (2- (N-5-n-decyl-) 2-perylenyl) aminopyridine), poly (2- (N-1-acridinyl) aminopyridine), poly (2- (N-2-acridinyl) aminopyridine), poly (2- (N-3-acridinyl) amino Lysine), poly (2- (N-4-acridinyl) aminopyridine), poly (2- (N-9-acridinyl) aminopyridine), poly (2- (N-1-methyl-9-acridinyl) aminopyridine) ), Poly (2- (N-1-ethyl-9-acridinyl) aminopyridine), poly (2- (N-1-n-hexyl-9-acridinyl) aminopyridine), poly (2- (N-1 -N-octyl-9-acridinyl) aminopyridine), poly (2- (N-1-n-decyl-9-acridinyl) aminopyridine), poly (2- (N-3-coumarinyl) aminopyridine), poly (2- (N-4-coumarinyl) aminopyridine), poly (2- (N-5-coumarinyl) aminopyridine), poly (2- (N-6-coumarinyl) aminopyridine), poly (2- (N 7-coumarinyl) aminopyridine), poly (2- (N-8-coumarinyl) aminopyridine), poly (2- (N-4-methyl-7-coumarinyl) aminopyridine), poly (2- (N-4 -Ethyl-7-coumarinyl) aminopyridine), poly (2- (N-4-n-hexyl-7-coumarinyl) aminopyridine), poly (2- (N-4-n-octyl-7-coumarinyl) amino Pyridine), poly (2- (N-4-n-decyl-7-coumarinyl) aminopyridine) and the like.

In the polyaminopyridines of the present invention, the substituents represented by R ¹ and R ² in the general formula (1), which is the repeating unit, may each be the same species in the same molecule between repetitions. It may be different or different.

  Further, the polyaminopyridines of the present invention may be ones in which the repeating units represented by the general formula (1) are discontinuously arranged. That is, the site | part which is not represented by General formula (1) may interpose between repeating units represented by General formula (1). Such polyaminopyridines can be produced, for example, by using 2,6-diaminopyridines and the like as described later.

  Furthermore, in the polyaminopyridines of the present invention, the bonding form of the repeating unit represented by the general formula (1) in the molecule may be a random copolymer form that is irregularly arranged in the molecular chain. It may also be a block copolymer system that is regularly arranged. In addition, from the viewpoint of obtaining high luminous efficiency, the bonding form is preferably a random copolymer pattern that is irregularly arranged.

  The number average molecular weight of the polyaminopyridines of the present invention is 500 to 1,000,000, preferably 1,000 to 100,000. When the number average molecular weight of polyaminopyridines is less than 500, the film formability may be deteriorated when the obtained solution is coated or cast. Moreover, when the number average molecular weight of polyaminopyridine exceeds 1000000, there exists a possibility that the solubility to a solvent may deteriorate and it may become difficult to use.

The polyaminopyridines of the present invention have a highly efficient light-emitting function because they have a site having a light-emitting property within the repeating unit and a site having a hole-transporting property as described later.
A light emission phenomenon such as fluorescence appears when, for example, a site having light emitting properties is excited by recombination of holes injected from the anode and electrons injected from the cathode, and then returns to the ground state.

The polyaminopyridines of the present invention include, for example, a moiety having a luminescent property which is a side chain represented by R ² in the general formula (1) and a positive chain other than the side chain represented by R ² in the general formula (1). Since the part having hole transporting properties is chemically bonded, the hole is efficiently transported to the part having light emitting properties. Furthermore, in the polyaminopyridines of the present invention, R ² in the general formula (1) may have a furyl group which may have a substituent, a thiophenyl group which may have a substituent, or a substituent. Even when the thiopyrenyl group, the pyrazinyl group which may have a substituent, and the pyridazinyl group which may have a substituent have only a side chain which does not have a light emitting function, the light emitting function Have. Although the details are unknown, when holes are generated on the imino group in the repeating unit, the side chain represented by R ² and the pyridine moiety of the main chain are conjugated, and the conjugation is high. It is thought to act over a wide range of the molecular main chain, and as is generally known, the conjugated structure in the molecule absorbs external energy such as light and electricity and exhibits a light emitting function it is conceivable that.

Therefore, the polyaminopyridines of the present invention can be obtained by variously selecting the substituents represented by R ¹ and R ² in the general formula (1) which is the repeating unit, and as described above. By discontinuously arranging the repeating units represented by (1) and appropriately selecting the bonding form of the repeating units, the light emission characteristics such as the emission color can be variously changed.

  As a method for producing the polyaminopyridines of the present invention, the general formula (2):

(Wherein R ¹ is the same as R ¹ in the general formula (1), and X represents a halogen atom) and the general formula (3):

(Wherein R ² is the same as R ² in the general formula (1)), a method of reacting a palladium compound and a phosphine compound as a catalyst in the presence of a base, and the like. It is done.

  In the 2,6-dihalogenopyridines represented by the general formula (2), examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  Specific examples of the 2,6-dihalogenopyridines represented by the general formula (2) include 2,6-difluoropyridine, 2,6-dichloropyridine, 2,6-dibromopyridine, Iodopyridine, 3-methyl-2,6-dichloropyridine, 4-methyl-2,6-dichloropyridine, 5-methyl-2,6-dichloropyridine, 3-ethyl-2,6-dichloropyridine, 4-ethyl -2,6-dichloropyridine, 5-ethyl-2,6-dichloropyridine, 3-isopropyl-2,6-dichloropyridine, 4-isopropyl-2,6-dichloropyridine, 5-isopropyl-2,6-dichloro Pyridine, 3-n-propyl-2,6-dichloropyridine, 4-n-propyl-2,6-dichloropyridine, 5-n-propyl-2,6-dichloropyridy 3-n-butyl-2,6-dichloropyridine, 4-n-butyl-2,6-dichloropyridine, 5-n-butyl-2,6-dichloropyridine, 3-sec-butyl-2,6- Dichloropyridine, 4-sec-butyl-2,6-dichloropyridine, 5-sec-butyl-2,6-dichloropyridine, 3-tert-butyl-2,6-dichloropyridine, 4-tert-butyl-2, 6-dichloropyridine, 5-tert-butyl-2,6-dichloropyridine, 3-n-pentyl-2,6-dichloropyridine, 4-n-pentyl-2,6-dichloropyridine, 5-n-pentyl- 2,6-dichloropyridine, 3-isopentyl-2,6-dichloropyridine, 4-isopentyl-2,6-dichloropyridine, 5-isopentyl-2,6-dichloro Lysine, 3-neopentyl-2,6-dichloropyridine, 4-neopentyl-2,6-dichloropyridine, 5-neopentyl-2,6-dichloropyridine, 3-n-hexyl-2,6-dichloropyridine, 4- n-hexyl-2,6-dichloropyridine, 5-n-hexyl-2,6-dichloropyridine, 3-isohexyl-2,6-dichloropyridine, 4-isohexyl-2,6-dichloropyridine, 5-isohexyl -2,6-dichloropyridine, 3-n-octyl-2,6-dichloropyridine, 4-n-octyl-2,6-dichloropyridine, 5-n-octyl-2,6-dichloropyridine, 3-n -Decyl-2,6-dichloropyridine, 4-n-decyl-2,6-dichloropyridine, 5-n-decyl-2,6-dichloropyridine, 4- And cyano-2,6-dichloropyridine and 4-methoxy-2,6-dichloropyridine. Among these, 2,6-dichloropyridine and 2,6-dibromopyridine are preferably used from the viewpoint of easy availability and economy.

On the other hand, the amine compound is a compound represented by the general formula (3). In the general formula (3), R ² is the same as R ² in the general formula (1).

Specific examples of the amine compound represented by the general formula (3) include 1-aminoperylene, 2-aminoperylene, 3-aminoperylene, 2-methyl-1-aminoperylene, 2-ethyl-1- Aminoperylene, 2-n-hexyl-1-aminoperylene, 2-n-octyl-1-aminoperylene, 2-n-decyl-1-aminoperylene, 3-methyl-1-aminoperylene, 3-ethyl-1 -Aminoperylene, 3-n-hexyl-1-aminoperylene, 3-n-octyl-1-aminoperylene, 3-n-decyl-1-aminoperylene, 4-methyl-1-aminoperylene, 4-ethyl- 1-aminoperylene, 4-n-hexyl-1-aminoperylene, 4-n-octyl-1-aminoperylene, 4-n-decyl-1-aminoperylene, 5-methyl-1 Aminoperylene, 5-ethyl-1-aminoperylene, 5-n-hexyl-1-aminoperylene, 5-n-octyl-1-aminoperylene, 5-n-decyl-1-aminoperylene, 6-methyl-1 -Aminoperylene, 6-ethyl-1-aminoperylene, 6-n-hexyl-1-aminoperylene, 6-n-octyl-1-aminoperylene, 6-n-decyl-1-aminoperylene, 7-methyl- 1-aminoperylene, 7-ethyl-1-aminoperylene, 7-n-hexyl-1-aminoperylene, 7-n-octyl-1-aminoperylene, 7-n-decyl-1-aminoperylene, 8-methyl -1-aminoperylene, 8-ethyl-1-aminoperylene, 8-n-hexyl-1-aminoperylene, 8-n-octyl-1-aminoperylene, 8-n-decyl -1-aminoperylene, 9-methyl-1-aminoperylene, 9-ethyl-1-aminoperylene, 9-n-hexyl-1-aminoperylene, 9-n-octyl-1-aminoperylene, 9-n- Decyl-1-aminoperylene, 10-methyl-1-aminoperylene, 10-ethyl-1-aminoperylene, 10-n-hexyl-1-aminoperylene, 10-n-octyl-1-aminoperylene, 10-n -Decyl-1-aminoperylene, 11-methyl-1-aminoperylene, 11-ethyl-1-aminoperylene, 11-n-hexyl-1-aminoperylene, 11-n-octyl-1-aminoperylene, 11- n-decyl-1-aminoperylene, 12-methyl-1-aminoperylene, 12-ethyl-1-aminoperylene, 12-n-hexyl-1-ami Noperylene, 12-n-octyl-1-aminoperylene, 12-n-decyl-1-aminoperylene, 1-methyl-2-aminoperylene, 1-ethyl-2-aminoperylene, 1-n-hexyl-2- Aminoperylene, 1-n-octyl-2-aminoperylene, 1-n-decyl-2-aminoperylene, 3-methyl-2-aminoperylene, 3-ethyl-2-aminoperylene, 3-n-hexyl-2 -Aminoperylene, 3-n-octyl-2-aminoperylene, 3-n-decyl-2-aminoperylene, 4-methyl-2-aminoperylene, 4-ethyl-2-aminoperylene, 4-n-hexyl- 2-aminoperylene, 4-n-octyl-2-aminoperylene, 4-n-decyl-2-aminoperylene, 5-methyl-2-aminoperylene, 5-ethyl-2- Minoperylene, 5-n-hexyl-2-aminoperylene, 5-n-octyl-2-aminoperylene, 5-n-decyl-2-aminoperylene, 6-methyl-2-aminoperylene, 6-ethyl-2- Aminoperylene, 6-n-hexyl-2-aminoperylene, 6-n-octyl-2-aminoperylene, 6-n-decyl-2-aminoperylene, 7-methyl-2-aminoperylene, 7-ethyl-2 -Aminoperylene, 7-n-hexyl-2-aminoperylene, 7-n-octyl-2-aminoperylene, 7-n-decyl-2-aminoperylene, 8-methyl-2-aminoperylene, 8-ethyl- 2-aminoperylene, 8-n-hexyl-2-aminoperylene, 8-n-octyl-2-aminoperylene, 8-n-decyl-2-aminoperylene, 9-methyl 2-aminoperylene, 9-ethyl-2-aminoperylene, 9-n-hexyl-2-aminoperylene, 9-n-octyl-2-aminoperylene, 9-n-decyl-2-aminoperylene, 10-methyl 2-aminoperylene, 10-ethyl-2-aminoperylene, 10-n-hexyl-2-aminoperylene, 10-n-octyl-2-aminoperylene, 10-n-decyl-2-aminoperylene, 11- Methyl-2-aminoperylene, 11-ethyl-2-aminoperylene, 11-n-hexyl-2-aminoperylene, 11-n-octyl-2-aminoperylene, 11-n-decyl-2-aminoperylene, 12 -Methyl-2-aminoperylene, 12-ethyl-2-aminoperylene, 12-n-hexyl-2-aminoperylene, 12-n-octyl-2 -Aminoperylene, 12-n-decyl-2-aminoperylene, 1-methyl-3-aminoperylene, 1-ethyl-3-aminoperylene, 1-n-hexyl-3-aminoperylene, 1-n-octyl- 3-aminoperylene, 1-n-decyl-3-aminoperylene, 2-methyl-3-aminoperylene, 2-ethyl-3-aminoperylene, 2-n-hexyl-3-aminoperylene, 2-n-octyl -3-aminoperylene, 2-n-decyl-3-aminoperylene, 4-methyl-3-aminoperylene, 4-ethyl-3-aminoperylene, 4-n-hexyl-3-aminoperylene, 4-n- Octyl-3-aminoperylene, 4-n-decyl-3-aminoperylene, 5-methyl-3-aminoperylene, 5-ethyl-3-aminoperylene, 5-n-hexyl- -Aminoperylene, 5-n-octyl-3-aminoperylene, 5-n-decyl-3-aminoperylene, 6-methyl-3-aminoperylene, 6-ethyl-3-aminoperylene, 6-n-hexyl- 3-aminoperylene, 6-n-octyl-3-aminoperylene, 6-n-decyl-3-aminoperylene, 7-methyl-3-aminoperylene, 7-ethyl-3-aminoperylene, 7-n-hexyl -3-aminoperylene, 7-n-octyl-3-aminoperylene, 7-n-decyl-3-aminoperylene, 8-methyl-3-aminoperylene, 8-ethyl-3-aminoperylene, 8-n- Hexyl-3-aminoperylene, 8-n-octyl-3-aminoperylene, 8-n-decyl-3-aminoperylene, 9-methyl-3-aminoperylene, 9-ethyl- -Aminoperylene, 9-n-hexyl-3-aminoperylene, 9-n-octyl-3-aminoperylene, 9-n-decyl-3-aminoperylene, 10-methyl-3-aminoperylene, 10-ethyl- 3-aminoperylene, 10-n-hexyl-3-aminoperylene, 10-n-octyl-3-aminoperylene, 10-n-decyl-3-aminoperylene, 11-methyl-3-aminoperylene, 11-ethyl -3-aminoperylene, 11-n-hexyl-3-aminoperylene, 11-n-octyl-3-aminoperylene, 11-n-decyl-3-aminoperylene, 12-methyl-3-aminoperylene, 12- Ethyl-3-aminoperylene, 12-n-hexyl-3-aminoperylene, 12-n-octyl-3-aminoperylene, 12-n-decyl -3-aminoperylene, 2-methoxy-1-aminoperylene, 2-methanoyl-1-aminoperylene, 2-carbamoyl-1-aminoperylene, 2-cyano-1-aminoperylene, 1-methoxy-2-aminoperylene 1-methanoyl-2-aminoperylene, 1-carbamoyl-2-aminoperylene, 1-cyano-2-aminoperylene, 1-aminoacridine, 2-aminoacridine, 3-aminoacridine, 4-aminoacridine, 9- Aminoacridine, 2-methyl-1-aminoacridine, 2-ethyl-1-aminoacridine, 2-n-hexyl-1-aminoacridine, 2-n-octyl-1-aminoacridine, 2-n-decyl-1 -Aminoacridine, 3-methyl-1-aminoacridine, 3-ethyl-1-aminoacridine, -N-hexyl-1-aminoacridine, 3-n-octyl-1-aminoacridine, 3-n-decyl-1-aminoacridine, 4-methyl-1-aminoacridine, 4-ethyl-1-aminoacridine, 4-n-hexyl-1-aminoacridine, 4-n-octyl-1-aminoacridine, 4-n-decyl-1-aminoacridine, 5-methyl-1-aminoacridine, 5-ethyl-1-aminoacridine 5-n-hexyl-1-aminoacridine, 5-n-octyl-1-aminoacridine, 5-n-decyl-1-aminoacridine, 6-methyl-1-aminoacridine, 6-ethyl-1-amino Acridine, 6-n-hexyl-1-aminoacridine, 6-n-octyl-1-aminoacridine, 6-n-decyl-1-aminoa Lysine, 7-methyl-1-aminoacridine, 7-ethyl-1-aminoacridine, 7-n-hexyl-1-aminoacridine, 7-n-octyl-1-aminoacridine, 7-n-decyl-1- Aminoacridine, 8-methyl-1-aminoacridine, 8-ethyl-1-aminoacridine, 8-n-hexyl-1-aminoacridine, 8-n-octyl-1-aminoacridine, 8-n-decyl-1 -Aminoacridine, 9-methyl-1-aminoacridine, 9-ethyl-1-aminoacridine, 9-n-hexyl-1-aminoacridine, 9-n-octyl-1-aminoacridine, 9-n-decyl- 1-aminoacridine, 1-methyl-2-aminoacridine, 1-ethyl-2-aminoacridine, 1-n-hexyl-2-aminoacridine Lysine, 1-n-octyl-2-aminoacridine, 1-n-decyl-2-aminoacridine, 3-methyl-2-aminoacridine, 3-ethyl-2-aminoacridine, 3-n-hexyl-2- Aminoacridine, 3-n-octyl-2-aminoacridine, 3-n-decyl-2-aminoacridine, 4-methyl-2-aminoacridine, 4-ethyl-2-aminoacridine, 4-n-hexyl-2 -Aminoacridine, 4-n-octyl-2-aminoacridine, 4-n-decyl-2-aminoacridine, 5-methyl-2-aminoacridine, 5-ethyl-2-aminoacridine, 5-n-hexyl- 2-aminoacridine, 5-n-octyl-2-aminoacridine, 5-n-decyl-2-aminoacridine, 6-methyl-2-amino Kridine, 6-ethyl-2-aminoacridine, 6-n-hexyl-2-aminoacridine, 6-n-octyl-2-aminoacridine, 6-n-decyl-2-aminoacridine, 7-methyl-2- Aminoacridine, 7-ethyl-2-aminoacridine, 7-n-hexyl-2-aminoacridine, 7-n-octyl-2-aminoacridine, 7-n-decyl-2-aminoacridine, 8-methyl-2 -Aminoacridine, 8-ethyl-2-aminoacridine, 8-n-hexyl-2-aminoacridine, 8-n-octyl-2-aminoacridine, 8-n-decyl-2-aminoacridine, 9-methyl- 2-aminoacridine, 9-ethyl-2-aminoacridine, 9-n-hexyl-2-aminoacridine, 9-n-octyl-2- Minoacridine, 9-n-decyl-2-aminoacridine, 1-methyl-3-aminoacridine, 1-ethyl-3-aminoacridine, 1-n-hexyl-3-aminoacridine, 1-n-octyl-3 -Aminoacridine, 1-n-decyl-3-aminoacridine, 2-methyl-3-aminoacridine, 2-ethyl-3-aminoacridine, 2-n-hexyl-3-aminoacridine, 2-n-octyl- 3-aminoacridine, 2-n-decyl-3-aminoacridine, 4-methyl-3-aminoacridine, 4-ethyl-3-aminoacridine, 4-n-hexyl-3-aminoacridine, 4-n-octyl -3-aminoacridine, 4-n-decyl-3-aminoacridine, 5-methyl-3-aminoacridine, 5-ethyl-3-amino Noacridine, 5-n-hexyl-3-aminoacridine, 5-n-octyl-3-aminoacridine, 5-n-decyl-3-aminoacridine, 6-methyl-3-aminoacridine, 6-ethyl-3- Aminoacridine, 6-n-hexyl-3-aminoacridine,
6-n-octyl-3-aminoacridine, 6-n-decyl-3-aminoacridine, 7-methyl-3-aminoacridine, 7-ethyl-3-aminoacridine, 7-n-hexyl-3-aminoacridine 7-n-octyl-3-aminoacridine, 7-n-decyl-3-aminoacridine, 8-methyl-3-aminoacridine, 8-ethyl-3-aminoacridine, 8-n-hexyl-3-amino Acridine, 8-n-octyl-3-aminoacridine, 8-n-decyl-3-aminoacridine, 9-methyl-3-aminoacridine, 9-ethyl-3-aminoacridine, 9-n-hexyl-3- Aminoacridine, 9-n-octyl-3-aminoacridine, 9-n-decyl-3-aminoacridine, 1-methyl-4-aminoacridy 1-ethyl-4-aminoacridine, 1-n-hexyl-4-aminoacridine, 1-n-octyl-4-aminoacridine, 1-n-decyl-4-aminoacridine, 2-methyl-4-amino Acridine, 2-ethyl-4-aminoacridine, 2-n-hexyl-4-aminoacridine, 2-n-octyl-4-aminoacridine, 2-n-decyl-4-aminoacridine, 3-methyl-4- Aminoacridine, 3-ethyl-4-aminoacridine, 3-n-hexyl-4-aminoacridine, 3-n-octyl-4-aminoacridine, 3-n-decyl-4-aminoacridine, 5-methyl-4 -Aminoacridine, 5-ethyl-4-aminoacridine, 5-n-hexyl-4-aminoacridine, 5-n-octyl-4-aminoa Lysine, 5-n-decyl-4-aminoacridine, 6-methyl-4-aminoacridine, 6-ethyl-4-aminoacridine, 6-n-hexyl-4-aminoacridine, 6-n-octyl-4- Aminoacridine, 6-n-decyl-4-aminoacridine, 7-methyl-4-aminoacridine, 7-ethyl-4-aminoacridine, 7-n-hexyl-4-aminoacridine, 7-n-octyl-4 -Aminoacridine, 7-n-decyl-4-aminoacridine, 8-methyl-4-aminoacridine, 8-ethyl-4-aminoacridine, 8-n-hexyl-4-aminoacridine, 8-n-octyl- 4-aminoacridine, 8-n-decyl-4-aminoacridine, 9-methyl-4-aminoacridine, 9-ethyl-4-aminoacridine Gin, 9-n-hexyl-4-aminoacridine, 9-n-octyl-4-aminoacridine, 9-n-decyl-4-aminoacridine, 1-methyl-5-aminoacridine, 1-ethyl-5- Aminoacridine, 1-n-hexyl-5-aminoacridine, 1-n-octyl-5-aminoacridine, 1-n-decyl-5-aminoacridine, 2-methyl-5-aminoacridine, 2-ethyl-5 -Aminoacridine, 2-n-hexyl-5-aminoacridine, 2-n-octyl-5-aminoacridine, 2-n-decyl-5-aminoacridine, 3-methyl-5-aminoacridine, 3-ethyl- 5-aminoacridine, 3-n-hexyl-5-aminoacridine, 3-n-octyl-5-aminoacridine, 3-n-decyl-5-a Noacridine, 4-methyl-5-aminoacridine, 4-ethyl-5-aminoacridine, 4-n-hexyl-5-aminoacridine, 4-n-octyl-5-aminoacridine, 4-n-decyl-5 Aminoacridine, 6-methyl-5-aminoacridine, 6-ethyl-5-aminoacridine, 6-n-hexyl-5-aminoacridine, 6-n-octyl-5-aminoacridine, 6-n-decyl-5 -Aminoacridine, 7-methyl-5-aminoacridine, 7-ethyl-5-aminoacridine, 7-n-hexyl-5-aminoacridine, 7-n-octyl-5-aminoacridine, 7-n-decyl- 5-aminoacridine, 8-methyl-5-aminoacridine, 8-ethyl-5-aminoacridine, 8-n-hexyl-5-a Noacridine, 8-n-octyl-5-aminoacridine, 8-n-decyl-5-aminoacridine, 9-methyl-5-aminoacridine, 9-ethyl-5-aminoacridine, 9-n-hexyl-5 Aminoacridine, 9-n-octyl-5-aminoacridine, 9-n-decyl-5-aminoacridine, 1-methyl-6-aminoacridine, 1-ethyl-6-aminoacridine, 1-n-hexyl-6 -Aminoacridine, 1-n-octyl-6-aminoacridine, 1-n-decyl-6-aminoacridine, 2-methyl-6-aminoacridine, 2-ethyl-6-aminoacridine, 2-n-hexyl- 6-aminoacridine, 2-n-octyl-6-aminoacridine, 2-n-decyl-6-aminoacridine, 3-methyl-6- Aminoacridine, 3-ethyl-6-aminoacridine, 3-n-hexyl-6-aminoacridine, 3-n-octyl-6-aminoacridine, 3-n-decyl-6-aminoacridine, 4-methyl-6 -Aminoacridine, 4-ethyl-6-aminoacridine, 4-n-hexyl-6-aminoacridine, 4-n-octyl-6-aminoacridine, 4-n-decyl-6-aminoacridine, 5-methyl- 6-aminoacridine, 5-ethyl-6-aminoacridine, 5-n-hexyl-6-aminoacridine, 5-n-octyl-6-aminoacridine, 5-n-decyl-6-aminoacridine, 7-methyl -6-aminoacridine, 7-ethyl-6-aminoacridine, 7-n-hexyl-6-aminoacridine, 7-n-octyl 6-aminoacridine, 7-n-decyl-6-aminoacridine, 8-methyl-6-aminoacridine, 8-ethyl-6-aminoacridine, 8-n-hexyl-6-aminoacridine, 8-n-octyl -6-aminoacridine, 8-n-decyl-6-aminoacridine, 9-methyl-6-aminoacridine, 9-ethyl-6-aminoacridine, 9-n-hexyl-6-aminoacridine, 9-n- Octyl-6-aminoacridine, 9-n-decyl-6-aminoacridine, 1-methyl-7-aminoacridine, 1-ethyl-7-aminoacridine, 1-n-hexyl-7-aminoacridine, 1-n -Octyl-7-aminoacridine, 1-n-decyl-7-aminoacridine, 2-methyl-7-aminoacridine, 2-ethyl- -Aminoacridine, 2-n-hexyl-7-aminoacridine, 2-n-octyl-7-aminoacridine, 2-n-decyl-7-aminoacridine, 3-methyl-7-aminoacridine, 3-ethyl- 7-aminoacridine, 3-n-hexyl-7-aminoacridine, 3-n-octyl-7-aminoacridine, 3-n-decyl-7-aminoacridine, 4-methyl-7-aminoacridine, 4-ethyl -7-aminoacridine, 4-n-hexyl-7-aminoacridine, 4-n-octyl-7-aminoacridine, 4-n-decyl-7-aminoacridine, 5-methyl-7-aminoacridine, 5- Ethyl-7-aminoacridine, 5-n-hexyl-7-aminoacridine, 5-n-octyl-7-aminoacridine, 5-n- Decyl-7-aminoacridine, 6-methyl-7-aminoacridine, 6-ethyl-7-aminoacridine, 6-n-hexyl-7-aminoacridine, 6-n-octyl-7-aminoacridine, 6-n -Decyl-7-aminoacridine, 8-methyl-7-aminoacridine, 8-ethyl-7-aminoacridine, 8-n-hexyl-7-aminoacridine, 8-n-octyl-7-aminoacridine, 8- n-decyl-7-aminoacridine, 9-methyl-7-aminoacridine, 9-ethyl-7-aminoacridine, 9-n-hexyl-7-aminoacridine, 9-n-octyl-7-aminoacridine, 9 -N-decyl-7-aminoacridine, 1-methyl-8-aminoacridine, 1-ethyl-8-aminoacridine, 1-n-he Sil-8-aminoacridine, 1-n-octyl-8-aminoacridine, 1-n-decyl-8-aminoacridine, 2-methyl-8-aminoacridine, 2-ethyl-8-aminoacridine, 2-n -Hexyl-8-aminoacridine, 2-n-octyl-8-aminoacridine, 2-n-decyl-8-aminoacridine, 3-methyl-8-aminoacridine, 3-ethyl-8-aminoacridine, 3- n-hexyl-8-aminoacridine, 3-n-octyl-8-aminoacridine, 3-n-decyl-8-aminoacridine, 4-methyl-8-aminoacridine, 4-ethyl-8-aminoacridine, 4 -N-hexyl-8-aminoacridine, 4-n-octyl-8-aminoacridine, 4-n-decyl-8-aminoacridine, -Methyl-8-aminoacridine, 5-ethyl-8-aminoacridine, 5-n-hexyl-8-aminoacridine, 5-n-octyl-8-aminoacridine, 5-n-decyl-8-aminoacridine, 6-methyl-8-aminoacridine, 6-ethyl-8-aminoacridine, 6-n-hexyl-8-aminoacridine, 6-n-octyl-8-aminoacridine, 6-n-decyl-8-aminoacridine 7-methyl-8-aminoacridine, 7-ethyl-8-aminoacridine, 7-n-hexyl-8-aminoacridine, 7-n-octyl-8-aminoacridine, 7-n-decyl-8-amino Acridine, 9-methyl-8-aminoacridine, 9-ethyl-8-aminoacridine, 9-n-hexyl-8-aminoacridine, 9 -N-octyl-8-aminoacridine, 9-n-decyl-8-aminoacridine, 1-methyl-9-aminoacridine, 1-ethyl-9-aminoacridine, 1-n-hexyl-9-aminoacridine, 1-n-octyl-9-aminoacridine, 1-n-decyl-9-aminoacridine, 2-methyl-9-aminoacridine, 2-ethyl-9-aminoacridine, 2-n-hexyl-9-aminoacridine 2-n-octyl-9-aminoacridine, 2-n-decyl-9-aminoacridine, 3-methyl-9-aminoacridine, 3-ethyl-9-aminoacridine, 3-n-hexyl-9-amino Acridine, 3-n-octyl-9-aminoacridine, 3-n-decyl-9-aminoacridine, 4-methyl-9-aminoacridine 4-ethyl-9-aminoacridine, 4-n-hexyl-9-aminoacridine, 4-n-octyl-9-aminoacridine, 4-n-decyl-9-aminoacridine, 5-methyl-9-aminoacridine 5-ethyl-9-aminoacridine, 5-n-hexyl-9-aminoacridine, 5-n-octyl-9-aminoacridine, 5-n-decyl-9-aminoacridine, 6-methyl-9-amino Acridine, 6-ethyl-9-aminoacridine, 6-n-hexyl-9-aminoacridine, 6-n-octyl-9-aminoacridine, 6-n-decyl-9-aminoacridine, 7-methyl-9- Aminoacridine, 7-ethyl-9-aminoacridine, 7-n-hexyl-9-aminoacridine, 7-n-octyl-9-aminoacridine Gin, 7-n-decyl-9-aminoacridine, 8-methyl-9-aminoacridine, 8-ethyl-9-aminoacridine, 8-n-hexyl-9-aminoacridine, 8-n-octyl-9- Aminoacridine, 8-n-decyl-9-aminoacridine, 2-methoxy-1-aminoacridine, 2-methanoyl-1-aminoacridine, 2-carbamoyl-1-aminoacridine, 2-cyano-1-aminoacridine, 1-methoxy-2-aminoacridine, 1-methanoyl-2-aminoacridine, 1-carbamoyl-2-aminoacridine, 1-cyano-2-aminoacridine, 3-aminocoumarin, 4-aminocoumarin, 5-aminocoumarin , 6-aminocoumarin, 7-aminocoumarin, 8-aminocoumarin, 4-methyl-3-amino Nocoumarin, 4-ethyl-3-aminocoumarin, 4-n-hexyl-3-aminocoumarin, 4-n-octyl-3-aminocoumarin, 4-n-decyl-3-aminocoumarin, 5-methyl-3- Aminocoumarin, 5-ethyl-3-aminocoumarin, 5-n-hexyl-3-
Aminocoumarin, 5-n-octyl-3-aminocoumarin, 5-n-decyl-3-aminocoumarin, 6-methyl-3-aminocoumarin, 6-ethyl-3-aminocoumarin, 6-n-hexyl-3 -Aminocoumarin, 6-n-octyl-3-aminocoumarin, 6-n-decyl-3-aminocoumarin, 7-methyl-3-aminocoumarin, 7-ethyl-3-aminocoumarin, 7-n-hexyl- 3-aminocoumarin, 7-n-octyl-3-aminocoumarin, 7-n-decyl-3-aminocoumarin, 8-methyl-3-aminocoumarin, 8-ethyl-3-aminocoumarin, 8-n-hexyl -3-aminocoumarin, 8-n-octyl-3-aminocoumarin, 8-n-decyl-3-aminocoumarin, 3-methyl-4-aminocoumarin, 3-ethyl-4- Minocoumarin, 3-n-hexyl-4-aminocoumarin, 3-n-octyl-4-aminocoumarin, 3-n-decyl-4-aminocoumarin, 5-methyl-4-aminocoumarin, 5-ethyl-4- Aminocoumarin, 5-n-hexyl-4-aminocoumarin, 5-n-octyl-4-aminocoumarin, 5-n-decyl-4-aminocoumarin, 6-methyl-4-aminocoumarin, 6-ethyl-4 -Aminocoumarin, 6-n-hexyl-4-aminocoumarin, 6-n-octyl-4-aminocoumarin, 6-n-decyl-4-aminocoumarin, 7-methyl-4-aminocoumarin, 7-ethyl- 4-aminocoumarin, 7-n-hexyl-4-aminocoumarin, 7-n-octyl-4-aminocoumarin, 7-n-decyl-4-aminocoumarin, 8-methyl 4-aminocoumarin, 8-ethyl-4-aminocoumarin, 8-n-hexyl-4-aminocoumarin, 8-n-octyl-4-aminocoumarin, 8-n-decyl-4-aminocoumarin, 3-methyl -5-aminocoumarin, 3-ethyl-5-aminocoumarin, 3-n-hexyl-5-aminocoumarin, 3-n-octyl-5-aminocoumarin, 3-n-decyl-5-aminocoumarin, 4- Methyl-5-aminocoumarin, 4-ethyl-5-aminocoumarin, 4-n-hexyl-5-aminocoumarin, 4-n-octyl-5-aminocoumarin, 4-n-decyl-5-aminocoumarin, 6 -Methyl-5-aminocoumarin, 6-ethyl-5-aminocoumarin, 6-n-hexyl-5-aminocoumarin, 6-n-octyl-5-aminocoumarin, 6-n-de Sil-5-aminocoumarin, 7-methyl-5-aminocoumarin, 7-ethyl-5-aminocoumarin, 7-n-hexyl-5-aminocoumarin, 7-n-octyl-5-aminocoumarin, 7-n -Decyl-5-aminocoumarin, 8-methyl-5-aminocoumarin, 8-ethyl-5-aminocoumarin, 8-n-hexyl-5-aminocoumarin, 8-n-octyl-5-aminocoumarin, 8- n-decyl-5-aminocoumarin, 3-methyl-6-aminocoumarin, 3-ethyl-6-aminocoumarin, 3-n-hexyl-6-aminocoumarin, 3-n-octyl-6-aminocoumarin, 3 -N-decyl-6-aminocoumarin, 4-methyl-6-aminocoumarin, 4-ethyl-6-aminocoumarin, 4-n-hexyl-6-aminocoumarin, 4-n-o Til-6-aminocoumarin, 4-n-decyl-6-aminocoumarin, 5-methyl-6-aminocoumarin, 5-ethyl-6-aminocoumarin, 5-n-hexyl-6-aminocoumarin, 5-n -Octyl-6-aminocoumarin, 5-n-decyl-6-aminocoumarin, 7-methyl-6-aminocoumarin, 7-ethyl-6-aminocoumarin, 7-n-hexyl-6-aminocoumarin, 7- n-octyl-6-aminocoumarin, 7-n-decyl-6-aminocoumarin, 8-methyl-6-aminocoumarin, 8-ethyl-6-aminocoumarin, 8-n-hexyl-6-aminocoumarin, 8 -N-octyl-6-aminocoumarin, 8-n-decyl-6-aminocoumarin, 3-methyl-7-aminocoumarin, 3-ethyl-7-aminocoumarin, 3-n-he Sil-7-aminocoumarin, 3-n-octyl-7-aminocoumarin, 3-n-decyl-7-aminocoumarin, 4-methyl-7-aminocoumarin, 4-ethyl-7-aminocoumarin, 4-n -Hexyl-7-aminocoumarin, 4-n-octyl-7-aminocoumarin, 4-n-decyl-7-aminocoumarin, 5-methyl-7-aminocoumarin, 5-ethyl-7-aminocoumarin, 5- n-hexyl-7-aminocoumarin, 5-n-octyl-7-aminocoumarin, 5-n-decyl-7-aminocoumarin, 6-methyl-7-aminocoumarin, 6-ethyl-7-aminocoumarin, 6 -N-hexyl-7-aminocoumarin, 6-n-octyl-7-aminocoumarin, 6-n-decyl-7-aminocoumarin, 8-methyl-7-aminocoumarin, 8-e Til-7-aminocoumarin, 8-n-hexyl-7-aminocoumarin, 8-n-octyl-7-aminocoumarin, 8-n-decyl-7-aminocoumarin, 3-methyl-8-aminocoumarin, 3 -Ethyl-8-aminocoumarin, 3-n-hexyl-8-aminocoumarin, 3-n-octyl-8-aminocoumarin, 3-n-decyl-8-aminocoumarin, 4-methyl-8-aminocoumarin, 4-ethyl-8-aminocoumarin, 4-n-hexyl-8-aminocoumarin, 4-n-octyl-8-aminocoumarin, 4-n-decyl-8-aminocoumarin, 5-methyl-8-aminocoumarin 5-ethyl-8-aminocoumarin, 5-n-hexyl-8-aminocoumarin, 5-n-octyl-8-aminocoumarin, 5-n-decyl-8-aminocoumarin, -Methyl-8-aminocoumarin, 6-ethyl-8-aminocoumarin, 6-n-hexyl-8-aminocoumarin, 6-n-octyl-8-aminocoumarin, 6-n-decyl-8-aminocoumarin, 7-methyl-8-aminocoumarin, 7-ethyl-8-aminocoumarin, 7-n-hexyl-8-aminocoumarin, 7-n-octyl-8-aminocoumarin, 7-n-decyl-8-aminocoumarin 3-methyl-8-aminocoumarin, 3-ethyl-8-aminocoumarin, 3-n-hexyl-8-aminocoumarin, 3-n-octyl-8-aminocoumarin, 3-n-decyl-8-amino Coumarin, 4-methyl-8-aminocoumarin, 4-ethyl-8-aminocoumarin, 4-n-hexyl-8-aminocoumarin, 4-n-octyl-8-aminocoumarin 4-n-decyl-8-aminocoumarin, 5-methyl-8-aminocoumarin, 5-ethyl-8-aminocoumarin, 5-n-hexyl-8-aminocoumarin, 5-n-octyl-8-aminocoumarin , 5-n-decyl-8-aminocoumarin, 6-methyl-8-aminocoumarin, 6-ethyl-8-aminocoumarin, 6-n-hexyl-8-aminocoumarin, 6-n-octyl-8-amino Coumarin, 6-n-decyl-8-aminocoumarin, 7-methyl-8-aminocoumarin, 7-ethyl-8-aminocoumarin, 7-n-hexyl-8-aminocoumarin, 7-n-octyl-8- Aminocoumarin, 7-n-decyl-8-aminocoumarin, 4-methoxy-3-aminocoumarin, 4-methanoyl-3-aminocoumarin, 4-carbamoyl-3-aminocouma Examples include phosphorus, 4-cyano-3-aminocoumarin, 3-methoxy-4-aminocoumarin, 3-methanoyl-4-aminocoumarin, 3-carbamoyl-4-aminocoumarin, 3-cyano-4-aminocoumarin, and the like. .

  Among these, 1-aminoperylene, 2-aminoperylene, 3-aminoperylene, 1-aminoacridine, 2-aminoacridine, 3 can be easily obtained from the viewpoint of obtaining polyaminopyridines having high luminous efficiency by reaction. -Aminoacridine, 4-aminoacridine, 9-aminoacridine, 3-aminocoumarin, 4-aminocoumarin, 5-aminocoumarin, 6-aminocoumarin, 7-aminocoumarin and 8-aminocoumarin are preferably used.

  The amount of the amine compound used is not particularly limited, but is desirably 0.5 to 1.5 mol, preferably 0.9 to 1.1 mol, based on 1 mol of 2,6-dihalogenopyridines. . When the usage-amount of an amine compound is less than 0.5 mol, there exists a possibility that reaction may become difficult to advance. Moreover, when the usage-amount of an amine compound exceeds 1.5 mol, there is no effect corresponding to a usage-amount and it is not economical.

  Examples of the palladium compound used in the reaction for obtaining the polyaminopyridines of the present invention include tetravalent palladium compounds such as sodium hexachloropalladium (IV) tetrahydrate and potassium hexachloropalladium (IV); Palladium (II), palladium bromide (II), palladium acetate (II), palladium acetylacetonate (II), dichlorobis (benzonitrile) palladium (II), dichlorobis (acetonitrile) palladium (II), dichlorobis (triphenylphosphine) ) Palladium (II), dichlorobis (tri-o-tolylphosphine) palladium (II), dichlorotetraammine palladium (II), dichloro (cycloocta-1,5-diene) palladium (II), palladium triflu Divalent palladium compounds such as diacetate (II); tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium chloroform complex (0), tetrakis (triphenylphosphine) palladium (0), etc. Examples include zerovalent palladium compounds. Among these, from the viewpoint of having high reaction activity, zero-valent palladium compounds are preferable, and among these, tris (dibenzylideneacetone) dipalladium (0) is preferably used.

  The amount of the palladium compound used is desirably 0.01 to 20 mol%, preferably 0.02 to 5 mol% in terms of palladium with respect to 2,6-dihalogenopyridines. When the usage-amount of a palladium compound is less than 0.01 mol%, there exists a possibility that reaction may become difficult to advance. Moreover, when the usage-amount of a palladium compound exceeds 20 mol%, there exists a possibility that it may not become economical without the effect corresponding to a usage-amount.

  Examples of the phosphine compound used in the reaction for obtaining the polyaminopyridines of the present invention include 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 1,1′-bis (diphenylphosphine). Fino) ferrocene, 9,9-dimethyl-4,5-bis (diphenylphosphino) xanthene, N, N′-dimethyl-1- [1 ′, 2-bis (diphenylphosphino) ferrocenyl], etc. Examples thereof include phosphine compounds having chelating ability as ligands. Among them, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl and 9,9-dimethyl-4,5-bis (diphenylphosphino) xanthene are preferably used from the viewpoint of having high reaction activity. It is done.

The amount of the phosphine compound used is 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of the palladium compound. When the usage-amount of a phosphine compound is less than 0.1 mol, there exists a possibility that reaction may become difficult to advance. Moreover, when the usage-amount of a phosphine compound exceeds 10 mol, there is no effect corresponding to the usage-amount and it is not economical.
The palladium compound and the phosphine compound may be added individually to the reaction system or may be prepared in the form of a complex in advance and added as a mixed catalyst containing them.

  Examples of the base used in the reaction for obtaining the polyaminopyridines of the present invention include sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, lithium tert-butoxide, sodium tert-butoxide, and potassium. And alkali metal alkoxides such as -tert-butoxide. These bases may be prepared from alkali metals, alkali metal hydrides, alkali metal hydroxides and alcohols and added to the reaction system.

  The amount of the base used is 2 mols or more, preferably 2 to 10 mols per mol of 2,6-dihalogenopyridines. When the usage-amount of a base is less than 2 mol, there exists a possibility that a yield may fall.

  In the present invention, the reaction is performed in an inert solvent. Examples of the inert solvent include aromatic hydrocarbon solvents such as benzene, toluene and xylene; ether solvents such as diethyl ether, tetrahydrofuran and dioxane; acetonitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphotri Examples include amides. Of these, aromatic hydrocarbon solvents such as benzene, toluene and xylene are preferably used because the solvent can be easily recycled.

  The reaction temperature is 20 to 250 ° C, preferably 50 to 150 ° C. When the reaction temperature is lower than 20 ° C, the reaction may take a long time. Moreover, when reaction temperature is higher than 250 degreeC, a side reaction occurs and there exists a possibility that a yield may fall. Although reaction time changes with reaction temperature, it is 1 to 20 hours normally.

  As described above, the polyaminopyridines of the present invention may be ones in which the repeating units represented by the general formula (1) are discontinuously arranged as necessary to obtain desired light emission characteristics. . Examples of the method for producing polyaminopyridines in which the repeating units are discontinuously arranged include, for example, 2,6-dihalogenopyridines represented by the general formula (2) and an amine represented by the general formula (3). In addition to the compound, general formula (4):

(Wherein R ³ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkanoyl group, a carbamoyl group or a cyano group, and Y represents an amino group) The method of making it react like the above using the appropriate quantity of a kind is mentioned.

  In the present invention, the bonding form of the repeating unit represented by the general formula (1) in the molecule of the polyaminopyridines may be a random copolymer form as described above, and is regularly arranged. It may be a block copolymer format. This binding form is generally greatly influenced by the reactivity of the 2,6-dihalogenopyridines used in the reaction, the amine compound and the optionally added 2,6-diaminopyridines. For example, when the mutual reactivity is relatively equal, there is a tendency that a random copolymer is produced. On the other hand, in the case where the reactivity is greatly different from each other, by increasing the amount of the less reactive one, the resulting polyaminopyridines can be combined in random and less regular forms.

  The polyaminopyridines thus obtained can be isolated, for example, by adding a mixed solvent of aqueous ammonia / methanol to precipitate the polyaminopyridines, filtering, washing, removing the catalyst, etc., and then drying. it can.

The polyaminopyridines of the present invention can be suitably used, for example, as a light emitter in an organic EL device.
The organic EL element has, for example, a structure in which a light emitting layer is sandwiched between an anode and a cathode. Specifically, first, a thin film made of a desired electrode material is formed on a substrate such as glass, transparent plastic or quartz to form an anode, and a light emitting layer made of a light emitting layer material including a light emitter is formed on the upper surface. Then, a thin film made of a desired electrode material is further formed on the upper surface thereof to form a cathode, thereby forming an organic EL element.

As the electrode material in the anode, metals, alloys, electrically conductive compounds and mixtures thereof having a large work function of, for example, 4 eV or more are preferable. For example, Au, CuI, ITO, SnO ₂ , ZnO and the like are preferably used. These electrode material thin films can be formed by vapor deposition, sputtering, or the like. When light emission is extracted from this electrode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as an electrode is several hundred Ω / Since the thickness is preferably equal to or less than mm, the film thickness is usually 10 nm to 1 μm, and preferably 10 nm to 200 nm.

  As a method of forming the light emitting layer on the upper surface of the anode, for example, a light emitting layer material containing a light emitter is made of tetrahydrofuran, N, N-dimethylformamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, toluene, benzene, chloroform. Examples of the coating method include a spin coating method and a casting method using a solution dissolved in a solvent such as the above. According to these methods, a homogeneous film with few pinholes can be obtained without unnecessarily impairing the light emitting function of the light emitter. The film thickness is not particularly limited, and is usually 2 nm to 5 μm.

As the electrode material in the cathode, metals, alloys, electrically conductive compounds and mixtures thereof having a work function as small as 4 eV or less are preferable, for example, sodium, magnesium, lithium, indium, sodium-potassium alloy, Al / AlO _2. A magnesium / copper mixture is preferably used. The method for forming a thin film of these electrode materials is the same as that for the anode, and the film thickness is usually 10 nm to 1 μm, preferably 50 nm to 200 nm.
By applying a direct current or alternating current voltage of, for example, 5 to 40 V to the organic EL element thus obtained, light emission from the transparent or translucent electrode side can be observed.

  In general, for the purpose of increasing the efficiency of light emission, the organic EL element is injected from a hole transport layer and / or a cathode for efficiently transmitting holes injected from the anode to the light emitting layer. It is useful to further provide an electron transport layer for efficiently transferring electrons to the light emitting layer. For example, as the thin film of the hole transport layer and the electron transport layer, the former is a hole transport material on the upper surface of the anode, the latter is an electron transport material on the upper surface of the light emitting layer, and the thin film of the electrode material is used. Each can be formed using the same method. In addition, a method of forming a light emitting layer using a light emitting layer material prepared by mixing the light emitter and a hole transport material or an electron transport material can achieve the same effect.

As the hole transport material, for example, a material having a hole mobility of at least 10 ⁻⁶ cm ² / V · sec or more when an electric field of 10 ⁴ to 10 ⁶ V / cm is applied is preferable. , Porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds.

  Specific examples of the electron transport material include anthraquinodimethane derivatives, fluorenylidenemethane derivatives, anthrone derivatives, oxadiazole derivatives, and thiophene derivatives.

  Since the polyaminopyridines of the present invention are excellent in solubility in various solvents, the light emitting layer can be formed by using the solution dissolved in the solvent as described above. At this time, for the purpose of imparting characteristics such as flexibility to the obtained film, various kinds of light emitting functions such as polymethyl methacrylate (PMMA) that do not significantly inhibit the light emitting function of the polyaminopyridines of the present invention are provided. These additives may be used in combination.

  Further, the polyaminopyridines of the present invention have a site having luminescence in the repeating unit and a site having a structure similar to the substance exemplified for the hole transport material, that is, a site having a hole transport property. Therefore, the necessity for providing the hole transport layer is reduced, and highly efficient light emission can be realized.

  For example, the polyaminopyridine of the present invention is used as a light emitter, and a mixture of this and an electron transport material such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline is used as a light emitting layer material. When the organic EL element is formed by forming a hole, the holes injected from the anode are molecules due to the effect of the site having hole transportability in the repeating unit widely distributed in the molecules of the polyaminopyridines of the present invention. It moves inward and moves between molecules by hopping conduction and is efficiently transported to a site having luminescence. And since it recombines efficiently with the electron inject | poured from the cathode and the electron transport material, highly efficient light emission is realizable.

  According to the present invention, polyaminopyridines having high luminous efficiency and a method for producing the same can be provided.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

Example 1
In a 1 L four-necked flask equipped with a condenser and a thermometer, 12.83 g (86.7 mmol) of 2,6-dichloropyridine, 13.97 g (86.7 mmol) of 3-aminocoumarin, Benzylideneacetone) dipalladium (0) 1.98 g (2.16 mmol), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl 4.05 g (6.50 mmol), sodium-tert- 25.0 g (260.1 mmol) of butoxide and 800 mL of toluene were charged. Subsequently, it heated up to 100 degreeC under nitrogen atmosphere, and was made to react at 100 degreeC for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature, the reaction solution was added to 2 L of 28 wt% ammonia water / methanol mixed solvent (volume ratio 1/4), and the precipitate was filtered off to obtain crude poly (2- (N- 3-coumarinyl) aminopyridine) was obtained. The obtained crude poly (2- (N-3-coumarinyl) aminopyridine) was washed with 0.5 L (volume ratio 1/4) of 28 wt% aqueous ammonia / methanol mixed solvent, further washed with methanol, By drying, 21.42 g of poly (2- (N-3-coumarinyl) aminopyridine) as a tan powder was obtained (yield 98.8%). Moreover, the number average molecular weight of the obtained poly (2- (N-3-coumarinyl) aminopyridine) was 2360. The number average molecular weight was measured at 30 ° C. in N, N-dimethylformamide containing LiBr (0.01 mol / L) using gel permeation chromatography (Tosoh Corporation, trade name: HLC-8020). It was calculated based on standard polystyrene.
The obtained poly (2- (N-3-coumarinyl) aminopyridine) could be identified from the following physical properties.
IR (KBr): 3400, 1755, 1608, 1574, 1417, 1291, 1178, 828, 774 (cm ⁻¹ )

Example 2
In Example 1, instead of 4.05 g (6.50 mmol) of 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 9,9-dimethyl-4,5-bis (diphenylphosphine) 21.52 g of poly (2- (N-3-coumarinyl) aminopyridine) as a tan powder was obtained in the same manner as in Example 1 except that 3.76 g (6.50 mmol) of fino) xanthene was used. (Yield 99.2%). Moreover, when the number average molecular weight was measured like Example 1, the number average molecular weight of the obtained poly (2- (N-3-coumarinyl) aminopyridine) was 2580.
The obtained poly (2- (N-3-coumarinyl) aminopyridine) could be identified from the following physical properties.
IR (KBr): 3405, 1747, 1618, 1574, 1412, 1291, 1180, 830, 774 (cm ⁻¹ )

Example 3
In Example 1, 1.98 g (2.16 mmol) of tris (dibenzylideneacetone) dipalladium (0) and 4.05 g of 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (6. Instead of 50 mmol) tris (dibenzylideneacetone) dipalladium (0) 0.20 g (0.22 mmol) and 9,9-dimethyl-4,5-bis (diphenylphosphino) xanthene 0.38 g (0 .65 mmol) was used in the same manner as in Example 1 to obtain 20.64 g of poly (2- (N-3-coumarinyl) aminopyridine) as a tan powder (yield 95.2%). ). Moreover, when the number average molecular weight was measured like Example 1, the number average molecular weight of the obtained poly (2- (N-3-coumarinyl) aminopyridine) was 2480.
The obtained poly (2- (N-3-coumarinyl) aminopyridine) could be identified from the following physical properties.
IR (KBr): 3405, 1747, 1618, 1574, 1412, 1291, 1180, 830, 774 (cm ⁻¹ )

Example 4
In Example 1, instead of 4.05 g (6.50 mmol) of 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 9,9-dimethyl-4,5-bis (diphenylphosphine) Fino) 3.76 g (6.50 mmol) of xanthene was replaced with 13.97 g (86.7 mmol) of 3-aminocoumarin, and 15.19 g (86.7 mmol) of 7-amino-4-methylcoumarin, respectively. Except that it was used, in the same manner as in Example 1, 22.25 g of poly (2- (N-4-methyl-7-coumarinyl) aminopyridine) as a tan powder was obtained (yield 97.1%). Moreover, when the number average molecular weight was measured like Example 1, the number average molecular weight of the obtained poly (2- (N-4-methyl-7-coumarinyl) aminopyridine) was 2930.
The obtained poly (2- (N-4-methyl-7-coumarinyl) aminopyridine) could be identified from the following physical properties.
IR (KBr): 3410, 1697, 1619, 1574, 1417, 1398, 1291, 1151, 1065, 833, 774 (cm ⁻¹ )

Example 5
In Example 1, instead of 4.05 g (6.50 mmol) of 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 9,9-dimethyl-4,5-bis (diphenylphosphine) Fino) 3.76 g (6.50 mmol) of xanthene was used in place of 13.97 g (86.7 mmol) of 3-aminocoumarin, except that 16.93 g (86.7 mmol) of 9-aminoacridine was used. In the same manner as in Example 1, 23.15 g of poly (2- (N-9-acridinyl) aminopyridine) as a tan powder was obtained (yield 93.9%). Moreover, when the number average molecular weight was measured like Example 1, the number average molecular weight of the obtained poly (2- (N-9-acridinyl) aminopyridine) was 3060.
The obtained poly (2- (N-9-acridinyl) aminopyridine) could be identified from the following physical properties.
IR (KBr): 3405, 1619, 1616, 1584, 1417, 1290, 1158, 784, 736 (cm ⁻¹ )

Example 6
In Example 1, instead of 4.05 g (6.50 mmol) of 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 9,9-dimethyl-4,5-bis (diphenylphosphine) Fino) 3.76 g (6.50 mmol) of xanthene was used in place of 13.97 g (86.7 mmol) of 3-aminocoumarin, and 23.18 g (86.7 mmol) of 2-aminoperylene was used. In the same manner as in Example 1, 27.80 g of poly (2- (N-2-perylenyl) aminopyridine) as a tan powder was obtained (yield 93.7%). Further, when the number average molecular weight was measured in the same manner as in Example 1, the number average molecular weight of the obtained poly (2- (N-2-perylenyl) aminopyridine) was 3280.
The obtained poly (2- (N-2-perylenyl) aminopyridine) could be identified from the following physical properties.
IR (KBr): 3406, 1575, 1484, 1411, 1382, 1298, 1146, 811, 772 (cm ⁻¹ )

Evaluation The energy level of the highest occupied orbital (HOMO) of electrons and the energy level of the lowest empty orbital (LUMO) of the polyaminopyridines obtained in Examples 1 to 6 and the difference between the energy levels (band gap energy) ) Was measured by the cyclic voltammetry (CV) method. Specifically, as a measurement sample, a 1-methyl-2-pyrrolidone solution of polyaminopyridines was cast on a platinum electrode, dried under reduced pressure at 80 ° C. for 5 hours to remove the solvent, and a thin film was formed on the electrode. It was. The energy levels of the highest occupied orbit and the lowest unoccupied orbit are determined by using this electrode and tetrabutylammonium tetrafluoroborate in acetonitrile by an electrochemical analyzer (BAS Co., Ltd., trade name: ALS model 600B electrochemical analyzer). A CV curve was measured with an electrolytic substrate (0.1 mol / L) and a reference electrode of Ag / Ag ⁺ at a scanning speed of 50 mV / sec at 25 ° C., and calculated from the oxidation potential and reduction potential. The results are shown in Table 1.

In addition, a 1-methyl-2-pyrrolidone solution of polyaminopyridines obtained in Examples 1 to 6 (concentration: 1.0 × 10 ⁻⁶ g / mL) was prepared, and the emission wavelength was measured with a fluorescence spectrophotometer (stock). It was measured by Hitachi Ltd., trade name F-2500). Further, the quantum yield was calculated using quinine sulfate (solvent: 1N sulfuric acid, quantum yield: 0.56) as a standard substance. This quantum yield is the ratio between the number of absorbed photons and the number of emitted photons by fluorescence, and gives the probability that the excited state is deactivated by fluorescence. The higher the quantum yield, the higher the luminous efficiency. means. The results are shown in Table 2.

From Tables 1 and 2, the polyaminopyridines obtained in Examples 1 to 6 have a suitable energy rank as a light emitter of the polymer organic EL device, have a suitable emission wavelength and a high quantum yield. You can see that

Claims (3)

General formula (1):

Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkanoyl group, a carbamoyl group or a cyano group, and R ² is a condensed polycyclic carbocyclic group which may have a substituent. Represents a monocyclic heterocyclic group which may have a substituent or a condensed polycyclic heterocyclic group which may have a substituent.), And has a number average molecular weight of 500 Polyaminopyridines in the range of ~ 1000000. ^2. The polyaminopyridine according to claim 1, wherein, in the general formula (1), R ¹ is a hydrogen atom, and R ² is a perylenyl group, an acridinyl group, or a coumarinyl group. General formula (2):

(Wherein R ¹ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkanoyl group, a carbamoyl group or a cyano group, and X represents a halogen atom) Pyridines and general formula (3):

Wherein R ² is a condensed polycyclic carbocyclic group which may have a substituent, a monocyclic heterocyclic group which may have a substituent, or a condensed polycyclic which may have a substituent. And a compound represented by the general formula (1), wherein the amine compound represented by formula (1) is reacted in the presence of a base with a palladium compound and a phosphine compound as catalysts.

(Wherein, ^{R 1} is the same as ^{R 1} in the general formula (2), ^{R 2} are the same as ^{R 2.} In the general formula (3)) has a repeating unit represented by the number A method for producing polyaminopyridines having an average molecular weight in the range of 500 to 1,000,000.