Aniline derivative and use thereof

Patent metadata

Field	Value
Publication number	US-2017012213-A1
Application number	US-201515125853-A
Country	US
Kind code	A1
Filing date	Mar 11, 2015
Priority date	Mar 14, 2014
Publication date	Jan 12, 2017
Grant date	—

Abstract

An aniline derivative represented by the formula, for instance, has good solubility in organic solvents, and when a thin film comprising such derivative as a charge-transporting substance is used in a hole injection layer, an organic EL element having excellent luminance characteristics can be obtained.

First claim

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

[wherein X is S, O, CH 2 or NCH 3 ;
each Ph 1 is independently a group of formula (P1)

(R 1 to R 4 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 and n are each independently integers from 0 to 5.]

2 . The aniline derivative of claim 1 , wherein R 1 to R 4 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 Ph 1 , X, m and n 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

• C07D209/88 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C09D5/24

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

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/636

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

• C07D403/14 Primary

  containing three or more hetero rings · CPC title