Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-10439145-B2
Application number	US-201314425373-A
Country	US
Kind code	B2
Filing date	Aug 6, 2013
Priority date	Sep 4, 2012
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

The present invention relates to compounds which are suitable for use in electronic devices, preferably organic electroluminescent devices.

First claim

The invention claimed is:

1. A compound of formula (I-1) or (III-1):

wherein
Ar 1 is on each occurrence, identically or differently, selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl, chrysenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or silafluorenyl, 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 , N(R 2 ) 2 , 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, each of which is optionally substituted by one or more radicals R 2 and wherein one or more CH 2 groups is 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 is optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 2 , and wherein two or more radicals R 1 optionally define a ring with one another;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 3 , CN, Si(R 3 ) 3 , N(R 3 ) 2 , 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, each of which is optionally substituted by one or more radicals R 3 and wherein one or more CH 2 groups is 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 the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 3 , and wherein two or more radicals R 2 optionally define a ring system with one another;
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 is optionally replaced by D or F; and wherein two or more radicals R 3 optionally define a ring system with one another;
X is C(R 1 ) 2 ; and
m, n, o, p, q, and r
are on each occurrence, identically or differently, 0 or 1; wherein when any one of m, n, o, p, q and r is 0, a group R 1 is bonded instead at the relevant positions to which the corresponding group X is bonded; and wherein the sum of m and n is 1, and the sum of o and p is 1, and the sum of q and r is 1.

2. 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 8 C atoms, or a branched or cyclic alkyl group having 3 to 8 C atoms, wherein the alkyl groups are optionally substituted by one or more radicals R 2 and wherein one or more CH 2 groups is optionally replaced by —C≡C—, —R 2 C═CR 2 —, Si(R 2 ) 2 , C═O, or —O—, or an aryl or heteroaryl group having 6 to 16 aromatic ring atoms optionally substituted by one or more radicals R 2 .

3. An oligomer, polymer, or dendrimer comprising one or more compounds of claim 1 , wherein the bond(s) to the polymer, oligomer or dendrimer are located at any desired positions in formulae (I-1) or (III-1) which are substituted by R 1 or R 2 .

4. A formulation comprising at least one polymer, oligomer, or dendrimer of claim 3 and at least one solvent.

5. An electronic device selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices, wherein said electronic device comprises at least one polymer, oligomer or dendrimer of claim 3 .

6. The electronic device of claim 5 , wherein said electronic device is an organic electroluminescent device and said at least one polymer, oligomer or dendrimer is employed as emitting material in an emitting layer.

7. A formulation comprising at least one compound of claim 1 and at least one solvent.

8. An electronic device selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices, wherein said electronic device comprises at least one compound of claim 1 .

9. The electronic device of claim 8 , wherein said electronic device is an organic electroluminescent devices and said at least one compound is employed as emitting material in an emitting layer.

10. A process for preparing the compound of claim 1 , wherein one or more organometallic coupling processes is employed.

Assignees

• Merck Patent Gmbh

Inventors

• Heil Holger
• Rodriguez Lara-Isabel
• Eckes Fabrice
• Kaufhold Oliver
• Gerhard Anja
• Riedmueller Stefan

Classifications

• C09K19/404

  containing boron or phosphorus · CPC title

• C07C229/52

  having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton · CPC title

• C09K19/3488

  the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines · CPC title

• C09K19/406

  containing silicon · CPC title

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title