Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9978949-B2
Application number	US-201314441975-A
Country	US
Kind code	B2
Filing date	Oct 18, 2013
Priority date	Nov 12, 2012
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The application relates to a compound of a formula (I) which is suitable for use as functional material in electronic devices.

First claim

The invention claimed is:

1. A compound of a formula (I)

where:
A is an arylamino group, optionally substituted by one or more radicals R 1 , or a carbazole group, optionally substituted by one or more radicals R 1 ;
E is a single bond;
X is O or S;
Z is on each occurrence, identically or differently, CR 2 ,
where, in the case where a group A is bonded to it, the group Z is equal to C;

R 1 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 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , where two or more radicals R 1 are optionally linked to one another and may form a ring;
R 2 is on each occurrence, identically or differently, H, D, F, CN, Si(R 3 ) 3 , a straight-chain alkyl having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═NR 3 , —C(═O)O—, —S— or —C(═O)NR 3 —, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , where two or more radicals R 2 are optionally linked to one another and may form a ring;
R 3 is on each occurrence, identically or differently, H, D, F, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms where the above-mentioned groups may each be substituted by one or more radicals R 4 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —S— or —C(═O)NR 4 —, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , where two or more radicals R 3 are optionally linked to one another and may form a ring;
R 4 is on each occurrence, identically or differently, H, D, F or an aliphatic radical having 1 to 20 C atoms, aromatic ring having 6 to 20 C atoms or heteroaromatic organic radical having 5 to 20 C atoms in which, in addition, one or more H atoms is optionally replaced by D or F; two or more substituents R 4 here are optionally linked to one another and may form a ring;
i is equal to 0 or 1; and
n is on each occurrence, identically or differently, 0 or 1, where the sum of all the indices n is equal to 1.

2. The compound according to claim 1 , wherein the group A is an arylamino group, which is optionally substituted by one or more radicals R 1 .

3. The compound according to claim 1 , wherein the compound contains only a single amino group.

4. The compound according to claim 1 , wherein X is equal to O.

5. The compound according to claim 1 , wherein the compound of the formula (I) conforms to one of the formulae (I-1) to (I-8)

where the symbols occurring are as defined in claim 1 .

6. An oligomer, polymer or dendrimer containing one or more compounds of the formula (I) according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any position in formula (I) that are substituted by R 1 or R 2 .

7. A formulation comprising at least one compound of the formula (I) according to claim 1 and at least one solvent.

8. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 6 and at least one solvent.

9. Electronic device comprising at least one compound of the formula (I) according to claim 1 .

10. The electronic device according to claim 9 , wherein the device is selected from the group consisting of organic integrated circuit (OIC), organic field-effect transistor (OFET), organic thin-film transistor (OTFT), organic light-emitting transistor (OLET), organic solar cell (OSC), organic optical detector, organic photoreceptor, organic field-quench device (OFQD), organic light-emitting electrochemical cell (OLEC), organic laser diode (O-laser) and organic electroluminescent device (OLED).

11. An organic electroluminescent device which comprises the compound of the formula (I) according to claim 1 , which is present in a hole-transport layer, an electron-blocking layer, a hole-injection layer or in an emitting layer.

Assignees

• Merck Patent Gmbh

Inventors

• Mujica-Fernaud Teresa
• Montenegro Elvira
• Voges Frank
• Kroeber Jonas Valentin
• Stoessel Philipp

Classifications

• C07D311/96

  spiro-condensed with carbocyclic rings or ring systems · CPC title

• H05B33/20

  characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title