Aniline derivatives and uses thereof

Patent metadata

Field	Value
Publication number	US-10147885-B2
Application number	US-201615552864-A
Country	US
Kind code	B2
Filing date	Feb 17, 2016
Priority date	Feb 24, 2015
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

Aniline derivatives such as those represented by the formulas shown, for example, have good solubility in organic solvents, and are able to provide organic electroluminescent elements having excellent longevity when thin films containing said aniline derivatives as charge transporting substances are used for hole injection layers.

First claim

The invention claimed is:

1. An aniline derivative of formula (1)

wherein Ph 1 is a group of formula (P1)

(wherein R 1 to R 4 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group or an alkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 20 carbon atoms, alkynyl group of 2 to 20 carbon atoms, aryl group of 6 to 20 carbon atoms or heteroaryl group of 2 to 20 carbon atoms which may be substituted with a halogen atom);
each Ar 1 is independently any moiety of formulas (A1) to (A34) below

(wherein R 5 to R 582 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a diphenylamino group, alkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 20 carbon atoms, alkynyl group of 2 to 20 carbon atoms, aryl group of 6 to 20 carbon atoms or heteroaryl group of 2 to 20 carbon atoms which may be substituted with a halogen atom;
each Ar 2 is independently an aryl group of 6 to 20 carbon atoms which may be substituted with a di(C 6-20 aryl)amino group;
R 583 is a hydrogen atom, an alkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 20 carbon atoms or alkynyl group of 2 to 20 carbon atoms which may be substituted with Z 1 , or an aryl group of 6 to 20 carbon atoms or heteroaryl group of 2 to 20 carbon atoms which may be substituted with Z 4 ;
R 584 and R 585 are each independently an aryl group of 6 to 20 carbon atoms or a heteroaryl group of 2 to 20 carbon atoms which may be substituted with Z 4 ;
Z 1 is a halogen atom, a nitro group, a cyano group, or an aryl group of 6 to 20 carbon atoms or heteroaryl group of 2 to 20 carbon atoms which may be substituted with Z 2 ; Z 2 is a halogen atom, a nitro group, a cyano group, or an alkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 20 carbon atoms or alkynyl group of 2 to 20 carbon atoms which may be substituted with Z 3 ; Z 3 is a halogen atom, a nitro group or a cyano group;
Z 4 is a halogen atom, a nitro group, a cyano group, or an alkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 20 carbon atoms or alkynyl group of 2 to 20 carbon atoms which may be substituted with Z 5 ; and
Z 5 is a halogen atom, a nitro group, a cyano group, or an aryl group of 6 to 20 carbon atoms or heteroaryl group of 2 to 20 carbon atoms which may be substituted with Z 3 ); and
k is an integer from 2 to 10.

2. The aniline derivative of claim 1 , wherein R 1 to R 4 are all hydrogen atoms.

3. The aniline derivative of claim 1 or 2 , wherein R 5 to R 582 are all hydrogen atoms.

4. A charge-transporting substance consisting of the aniline derivative of claim 1 .

5. A charge-transporting material comprising the charge-transporting substance of claim 4 .

6. A charge-transporting varnish comprising the charge-transporting substance of claim 4 and an organic solvent.

7. The charge-transporting varnish of claim 6 , further comprising a dopant substance.

8. The charge-transporting varnish of claim 7 , wherein the dopant substance is an arylsulfonic acid compound.

9. A charge-transporting thin film produced using the charge-transporting varnish of any one of claims 6 to 8 .

10. An organic electroluminescent device comprising the charge-transporting thin film of claim 9 .

11. A method for producing a charge-transporting thin film, comprising the step of coating a substrate with the charge-transporting varnish of any one of claims 6 to 8 and evaporating off the solvent.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Nakaie Naoki
• Nakazawa Taichi
• TERAI Seiya

Classifications

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C07C211/58

  Naphthylamines; N-substituted derivatives thereof · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title

• C09D5/24

  Electrically-conducting paints {(conductive materials H01B1/00)} · CPC title

• C07C2603/97

  containing five-membered rings · CPC title