Aniline derivatives and uses thereof

Patent metadata

Field	Value
Publication number	US-10700283-B2
Application number	US-201415026821-A
Country	US
Kind code	B2
Filing date	Oct 3, 2014
Priority date	Oct 4, 2013
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

Aniline derivatives such as those represented by the formula shown, for example, have good solubility with respect to organic solvents, and are able to provide an organic electroluminescent element having excellent luminance characteristics when a thin film containing said aniline derivatives is used as a charge transporting substance in a hole injection layer.

(In the formula, DPA represents a diphenylamino group.)

First claim

The invention claimed is:

1. An aniline derivative represented by the formula (1) or (2):

wherein R 1 and R 2 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom,
Ph 1 represents a group represented by the formula (P1):

wherein R 3 to R 6 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom,
Ar 1 independently represents a group represented by any of the formulas (B1) to (B11):

wherein R 7 to R 27 , R 30 to R 51 and R 53 to R 154 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a diphenylamino group, alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom,
R 28 and R 29 independently represent an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
R 52 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
Ar 4 independently represents an aryl group having 6 to 20 carbon atoms which may be substituted with a di(aryl groups having 6 to 20 carbon atoms)amino group,
Z 1 represents a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 2 ,
Z 2 represents a halogen atom, a nitro group, a cyano group, or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 3 ,
Z 3 represents a halogen atom, a nitro group or a cyano group,
Z 4 represents a halogen atom, a nitro group, a cyano group, or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 5 , and
Z 5 represents a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 3 ,
Ar 2 independently represents a group represented by any of the formulas (A1) to (A5) or (A7) to (A12) or (A14) to (A18):

wherein R 155 represents an hydrogen atom or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
R 156 and R 157 independently represent an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
DPA represents a diphenylamino group, and
Ar 4 , Z 1 and Z 3 to Z 5 have the same meanings as above,
Ar 3 represents a group represented by any of the formulas (C2) to (C8):

letter k represents an integer of 1 to 10, and
letter l represents 1 or 2.

2. The aniline derivative of claim 1 ,
wherein Ar 1 is a group represented by any of the formulas (B1′) to (B11′):

wherein R 7 to R 154 and Ar 4 have the same meanings as above, and
Ar 3 is a group represented by any of the formulas (C2′) to (C8′):

wherein DPA has the same meaning as above.

3. The aniline derivative of claim 1 or 2 , wherein the R 3 to R 6 , R 7 to R 27 , R 30 to R 51 and R 53 to R 154 are each a hydrogen atom.

4. The aniline derivative of claim 1 , represented by the formula (1-1):

wherein Ar 5 simultaneously represent a group represented by any of the formulas (D1), (D2), (D4) to (D9), or (D11) to (D13), and Ph 1 and letter k have the same meanings as above:

wherein R 52 , R 156 , R 157 , A 4 and DPA have the same meanings as above.

5. The aniline derivative of claim 1 , represented by the formula (1-3), (1-4), (1-9) or (1-10):

wherein Ar 51 represents a group represented by the formula (F1-1), Ar 52 represents a group represented by the formula (F2-1), Ar 71 represents a group represented by the formula (F2-2), Ar 72 represents a group represented by the formula (F1-2), and Ph 1 , Ar 1 and letter k have the same meanings as above:

wherein Cb 155 represents an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 , and Z 1 , Z 4 and Ar 4 have the same meanings as above.

6. The aniline derivative of claim 1 , represented by the formula (1-5), (1-6), (1-11) or (1-12):

wherein Ar 51 represents a group represented by the formula (

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Nakaie Naoki
• Nakazawa Taichi

Classifications

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title