Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-10424739-B2
Application number	US-201815987533-A
Country	US
Kind code	B2
Filing date	May 23, 2018
Priority date	Dec 12, 2011
Publication date	Sep 24, 2019
Grant date	Sep 24, 2019

Abstract

The invention relates to arylamino compounds and to the use thereof in electronic devices, for example organic electroluminescent devices. The invention furthermore relates to electronic devices comprising one or more of the said compounds, for example as hole-transport materials in a corresponding functional layer of the device. The invention furthermore relates to a process for the preparation of the said compounds, and to a formulation comprising one or more of the said compounds.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
Z is on each occurrence, identically or differently, CR 1 , wherein Z is C if a group Ar 1 or Ar 2 is bonded thereto;
W is CH;
Ar 1 is on each occurrence, identically or differently, an aromatic ring system having 6 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 1 or a heteroaromatic ring system having 6 to 30 aromatic ring atoms and selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, each of which is optionally substituted by one or more radicals R 1 ;
Ar 2 is on each occurrence, identically or differently, an aromatic ring system having 6 to 24 aromatic ring atoms optionally substituted by one or more radicals R 1 or a heteroaromatic ring system having 6 to 24 aromatic ring atoms and selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, each of which is optionally substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 2 , CN, Si(R 2 ) 3 , NO 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R 2 , wherein one or more CH 2 groups of said groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═S, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in said groups are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, which in each case is optionally substituted by one or more radicals R 2 ;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 3 , CN, Si(R 3 ) 3 , NO 2 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are each optionally substituted by one or more radicals R 3 , wherein one or more CH 2 groups in said groups are optionally replaced by —R 3 C═CR 3 , —C≡C—, Si(R 3 ) 2 , C═O, C═S, —C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in said groups are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, which in each case is optionally substituted by one or more radicals R 3 ;
R 3 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F;
n is on each occurrence, identically or differently, 0, 1, 2, 3, 4 or 5, wherein the sum of all indices n is at least 2;
m is 0, 1, 2 or 3;
wherein the three groups which are bonded to the central nitrogen atom, regarded as a whole, are not all identical; and
wherein at least one group Ar 1 and Ar 2 is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, each of which is optionally substituted by one or more radicals R 1 .

2. The compound of claim 1 , wherein said compound contains no further arylamino group apart from the triarylamino group depicted in formula (I).

3. The compound of claim 1 , wherein at least one group Ar 1 and Ar 2 is selected from the group consisting of dibenzofuran and dibenzothiophene, each of which is optionally substituted by one or more radicals R 1 .

4. The compound of claim 1 , wherein
R 1 is on each occurrence, identically or differently, H, D, F, CN, Si(R 2 ) 3 , a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein said groups are each optionally substituted by one or more radicals R 2 , or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, which in each case is optionally substituted by one or more radicals R 2 ; and
R 2 is on each occurrence, identically or differently, H, D, F, CN, Si(R 3 ) 3 , a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein said groups are each optionally substituted by one or more radicals R 3 , or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole, which in each case is optionally substituted by one or more radicals R 3 .

5. The compound of claim 1 , wherein
Z is CH if no group Ar 1 or Ar 2 is bonded thereto;
Z is C if a group Ar 1 or Ar 2 is bonded thereto; and
n is, identically or differently on each occurrence, 0 or 1.

6. The compound of claim 1 , wherein Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms optionally substituted by one or more radicals R 1 , wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole.

7. The compound of claim 1 , wherein at least one Ar 1 is bonded to the six-membered ring in the meta-position to the bond to the central nitrogen atom.

8. The compound of claim 1 , wherein Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 6 to 12 aromatic ring atoms optionally substituted by one or more radicals R 1 , wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole.

9. The compound of claim 1 , wherein n is 1 or 2.

10. The compound of claim 1 , wherein m is 0.

11. The compound of claim 1 , wherein no group Ar 1 is bonded on the six-membered ring in the ortho-position to the bond to the central nitrogen atom.

12. The compound of claim 1 , wherein said compound is selected from the group consisting of compounds of formulae (I-1) through (I-12):

wherein
Ar 1A , Ar 1B , Ar 1C , and Ar 1D
are on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms optionally substituted by one or more radicals R 1 , wherein the heteroaromatic ring system is selected from the group consisting of dibenzofuran, dibenzothiophene, and carbazole;

Ar 2A and Ar 2B
are on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms optionally substituted by one or

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Voges Frank
• Buesing Arne
• Pflumm Christof
• Mujica-Fernaud Teresa
• Wirges Christian

Classifications

• C07C211/54 Primary

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

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0059 Primary

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic