Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-10141518-B2
Application number	US-201715447882-A
Country	US
Kind code	B2
Filing date	Mar 2, 2017
Priority date	Apr 18, 2011
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

The present invention relates to a compound of the formula (I), to the use of this compound in an electronic device, and to an electronic device comprising one or more compounds of the formula (I). The invention furthermore relates to the preparation of the compound of the formula (I) and to a formulation comprising one or more compounds of the formula (I).

First claim

The invention claimed is:

1. A compound of a formula (I)

wherein A is, identically or differently on each occurrence, a group of the following formula (II) or (III)

wherein the dashed line emanating from the nitrogen atom represents the bond from the group A to the central benzene ring;
wherein the group HetAr including the nitrogen atom shown is, identically or differently on each occurrence, a heteroaryl group having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 ;
wherein the group Ar 1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 , and wherein the two groups Ar 1 may be connected via a group Y so that a ring is formed with the nitrogen atom of the group A, wherein
Y is selected from a single bond, BR 2 , C(R 2 ) 2 , Si(R 2 ) 2 , NR 2 , PR 2 , P(═O)R 2 , P(═S)R 2 , O, S, S═O, and S(═O) 2 ; and
R 1 is, identically or differently on each occurrence, CN, C(═O)R 3 , C(═O)OR 3 , C(═O)N(R 3 ) 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , S(═O)R 3 , S(═O) 2 R 3 , or a heteroaryl group selected from pyridyl, pyrazinyl, pyridazinyl, pyrimidyl and triazinyl, each of which optionally substituted by one or more radicals R 3 ;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, 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 the above-mentioned groups are optionally substituted by one or more radicals R 3 and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 3 C═CR 3 —, 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 are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , wherein two or more radicals R 2 are optionally linked to one another and optionally form a ring;
R 3 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 4 ) 2 , CHO, C(═O)R 4 , CR 4 ═C(R 4 ) 2 , CN, C(═O)OR 4 , C(═O)N(R 4 ) 2 , Si(R 4 ) 3 , N(R 4 ) 2 , NO 2 , P(═O)(R 4 ) 2 , OSO 2 R 4 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , 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 the above-mentioned groups are optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═S, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in the above-mentioned groups are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , wherein two or more radicals R 3 are optionally linked to one another and optionally form a ring; and
R 4 is, identically or differently on each occurrence, H, D, F, or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms are optionally replaced by D or F; two or more substituents R 4 are optionally linked to one another and optionally form a ring.

2. The compound of claim 1 , wherein the groups Ar 1 of group A of formula (II) are identically or differently on each occurrence, an aryl group having 6 to 10 aromatic ring atoms.

3. The compound of claim 1 , wherein the group A is identically or differently on each occurrence, of the formula (II), and each of the groups Ar 1 are connected via the group Y.

4. The compound of claim 1 , wherein the group of the formula (II) is a group of the following formulae (II-1) to (II-11):

wherein
Z is, identically or differently on each occurrence, CR 2 or N; and
Y is selected from a single bond, BR 2 , C(R 2 ) 2 , Si(R 2 ) 2 , NR 2 , PR 2 , P(═O)R 2 , O, S, S═O, or S(═O) 2 .

5. The compound of claim 1 , wherein the group of the formula (III) is selected from the formulae (III-1) to (III-3):

wherein
Z is, identically or differently on each occurrence, CR 2 or N.

6. The compound of claim 1 , wherein Y is selected from a single bond, C(R 2 ) 2 , NR 2 , O, or S.

7. The compound of claim 3 , wherein Y is selected from a single bond, C(R 2 ) 2 , NR 2 , O, or S.

8. The compound of claim 1 , wherein the group R 1 is CN.

9. The compound of claim 1 , wherein the radicals R 1 in formula (I) are selected identically.

10. The compound of claim 8 , wherein the radicals R 1 in formula (I) are selected identically.

11. A process for the preparation of the compound of claim 1 ,
wherein
at least one intermediate of a formula (Z)

is reacted with at least one arylamino compound, or at least one heterocyclic compound containing at least one NH function, and
X is, identically or differently on each occurrence, any reactive group.

12. An oligomer, polymer, or dendrimer, comprising one or more compounds of claim 1 , wherein bonds to the oligomer, polymer, or dendrimer, are connected at any position of the formula (I) by R 1 , R 2 , or R 3 .

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

14. A formulation comprising at least one oligomer, polymer, or dendrimer, of claim 10 and at least one solvent.

15. An electronic device comprising at least one compound of claim 1 , wherein the the electronic device is selected from an organic integrated circuit (O-IC), organic field-effect transistor (O-FET), organic thin-film transistor (O-TFT), organic light-emitting transistor (O-LET), organic solar cell (O-SC), organic optical detector, organic photoreceptor, organic field-quench device (O-FQD), light-emitting electrochemica

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Buesing Arne
• Voges Frank
• Pflumm Christof
• Parham Amir
• Eberle Thomas
• Mujica-Fernaud Teresa

Classifications

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• C07C217/92

  the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring · CPC title

• H01L51/0058

  Electricity · mapped topic

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title