Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-10651389-B2
Application number	US-201414901140-A
Country	US
Kind code	B2
Filing date	Jun 11, 2014
Priority date	Jul 2, 2013
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

The present invention relates to a compound of a formula (I), in which an electron-deficient group and an arylamino group are connected to one another via an intermediate group. The compound of the formula (I) is suitable as functional material in electronic devices.

First claim

The invention claimed is:

1. A compound of the formula (I)

where:
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system selected from the groups of the formula (Ar 1 -1) to (Ar 1 10) and (Ar 1 -14) to (Ar 1 -17),which may be substituted by one or more radicals R 2

Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 12 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 2 , where the aromatic ring system contains no condensed aryl or heteroaryl group having more than 10 aromatic ring atoms;
R 1 , R 2 are 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 , OR 3 , 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 may be 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 , 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 , where two or more radicals R 2 may be linked to one another and may form a ring;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 3 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , 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 4 and where one or more CH 2 groups in the above-mentioned groups may be replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)OR), —O—, —S—, SO or SO 2 , 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 4 , where two or more radicals R 3 may be linked to one another and may form a ring;
R 4 is on each occurrence, identically or differently, H, D, F or an aliphatic, heteroaliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F; two or more substituents R 4 here may be linked to one another and may form a ring;
n is equal to 1, 2, 3 or 4;
with the proviso that the following is excluded:
when n=1, the group Ar 1 is a group of the formula (Ar 1 -1) or (Ar 1 -14), and
when n=2, both groups Ar 1 correspond to a group of the formula (Ar 1 -1).

2. The compound according to claim 1 , wherein the compound contains precisely one amino group.

3. The compound according to claim 1 , wherein the compound contains precisely one triazine group.

4. The compound according to claim 1 , wherein the compound contains no condensed aryl group having more than 14 aromatic ring atoms.

5. The compound according to claim 1 , wherein R 1 is selected on each occurrence, identically or differently, from CN, an alkyl group having 1 to 10 C atoms or an alkenyl group having 2 to 10 C atoms, where the above-mentioned groups may be substituted by one or more radicals R 3 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 3 .

6. An oligomer, polymer or dendrimer containing one or more compounds according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer may be localised at any positions in formula (I) which are substituted by R 1 or R 2 .

7. A formulation comprising at least one compound 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. An electronic device comprising the compound according to claim 1 .

10. An electronic device comprising anode, cathode and at least one organic layer, where the organic layer comprises at least one compound according to claim 1 .

11. The electronic device according to claim 9 , wherein the device is selected from the group consisting of organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs).

12. An organic electroluminescent device comprising the compound according to claim 1 is employed as matrix material in an emitting layer in combination with one or more emitter compounds.

13. A compound of the formula (I)

where:
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system selected from the groups of the formula (Ar 1 -1) to (Ar 1 10) and (Ar 1 -14) to (Ar 1 -17), which may be substituted by one or more radicals R 2

Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 2 ,
where at least one group Ar 2 in the compound of the formula (I) represents a group Ar 2 *;

Ar 2 * is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 12 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 2 , where the aromatic ring system contains no condensed aryl or heteroaryl group having more than 10 aromatic ring atoms;
R 1 , R 2 are 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 , OR 3 , 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 may be replaced by —R 3 C═CR 3 —, —C≡C—, Si(R′) 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 , 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 , where two or more radicals R 2 may be linked to one another and may form a ring;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 3 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , a straig

Assignees

• Merck Patent Gmbh

Inventors

• Jatsch Anja
• Pflumm Christof
• Eberle Thomas
• Parham Amir Hossain
• Kroeber Jonas Valentin
• Stoessel Philipp
• Kaiser Joachim

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C09K2211/1014

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