Aniline derivative and use thereof

Patent metadata

Field	Value
Publication number	US-2017005271-A1
Application number	US-201515125835-A
Country	US
Kind code	A1
Filing date	Mar 11, 2015
Priority date	Mar 14, 2014
Publication date	Jan 5, 2017
Grant date	—

Abstract

Aniline derivatives such as are represented by, e.g., the formula have excellent solubility in organic solvents and make it possible to obtain an organic EL element having exceptional brightness characteristics when a thin film containing these derivatives as a charge transport material is applied to a hole injection layer.

First claim

1 . An aniline derivative characterized by having formula (1)

wherein R I to R 5 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 Ph 1 is independently a group of formula (P1)

(R 6 to R 9 being 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 a group having any of formulas (A1) to (A14);

and m is an integer from 1 to 5.

2 . The aniline derivative of claim 1 , wherein R 1 to R 9 are all hydrogen atoms.

3 . The aniline derivative of claim 1 , wherein each Ar 1 is independently a group having any of formulas (A1) to (A12).

4 . The aniline derivative of claim 3 , wherein each Ar 1 is independently a group having any of formulas (A1) to (A3), (A5) to (A7) and (A10) to (A12).

5 . The aniline derivative of claim 1 , wherein the Ar 1 moieties are all identical groups.

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

7 . A charge-transporting material comprising the charge-transporting substance of claim 6 .

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

9 . The charge-transporting varnish of claim 8 which further comprises a dopant substance.

10 . The charge-transporting varnish of claim 9 , wherein the dopant substance comprises a halotetracyanoquinodimethane compound.

11 . The charge-transporting varnish of claim 10 , wherein the dopant substance further comprises a heteropolyacid.

12 . A charge-transporting thin-film produced using the charge-transporting varnish of claim 8 .

13 . An electronic device comprising the charge-transporting thin-film of claim 12 .

14 . An organic electroluminescent device comprising the charge-transporting thin-film of claim 12 .

15 . A method of producing a charge-transporting thin-film, which method is characterized by comprising the step of coating a substrate with the charge-transporting varnish of claim 8 and evaporating off the solvent.

16 . A method of preparing the aniline derivative of claim 1 , which method is characterized by comprising the step of reacting an amine compound of formula (2)

(wherein R 1 to R 5 , Ph 1 and m are as defined above) with an aryl compound of formula (3)
[Chemical Formula 5]
Ar 1 —Z   (3)

(wherein Z is a halogen atom or a pseudo-halogen group, and Ar 1 is as defined above) in the presence of a catalyst.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Nakaie Naoki
• Nakazawa Taichi

Classifications

• C09D5/24

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

• C09K11/06

  containing organic luminescent materials · CPC title

• C07C211/54 Primary

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• C07C209/10 Primary

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title