Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-10056549-B2
Application number	US-201214115118-A
Country	US
Kind code	B2
Filing date	Apr 14, 2012
Priority date	May 5, 2011
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

The present invention relates to a compound of the formula (I), to the use of the compound in an electronic device, and to an electronic device comprising a compound of the formula (I). The present invention furthermore relates to a process for the preparation of a 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 (1-A-1) or formula (1-A-2)

where the following applies to the symbols and indices occurring:
Ar* is on each occurrence, identically or differently, an aromatic ring system having 6 to 24 aromatic ring atoms selected from the formulae (A-1) to (A-20)

wherein R 2 in formulae (A-17) to (A-20), is identically or differently H, alkyl groups having 1 to 20 C atoms, or phenyl; or an electron-rich heteroaryl group having 5 to 18 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 2′ ;

L is on each occurrence a single bond;
R 1 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, 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═S, 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, CN or NO 2 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , where two or more non-aromatic radicals R 1 is optionally linked to one another and may form a ring;
R 2′ is on each occurrence H;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 4 , CN, Si(R 4 ) 3 , NO 2 , P(═O)(R 4 ) 2 , 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, 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═S, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —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, CN or NO 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 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , where two or more radicals R 3 is optionally linked to one another and optionally forms a ring;
R 4 is on each occurrence, identically or differently, 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 is optionally replaced by D or F; two or more substituents R 4 here is optionally linked to one another and may form a ring;
where the compound does not contain a carbazole group; and
where at least one group Ar* which represents an electron-rich heteroaryl group having 5 to 18 aromatic ring atoms or an aromatic ring system having 12 to 24 aromatic ring atoms must be present in the compound.

2. The compound according to claim 1 , wherein
a) the group Ar* conforms to the following formula (H)

where
Y is NR 2 , PR 2 , O or S; and
p is on each occurrence equal to 0 or 1, where, for p=0, radicals R 2 are bonded at the relevant positions, and where, for Y═NR 2 , the two indices p cannot both be equal to 1;
the group is substituted by radicals R 2 at all free positions, and
the group R 2 is as defined in claim 1 , and
the group is optionally connected to the group L at any position, where the bonding may also occur at the site of the bond NR 2 or PR 2 ; or
b) the group Ar* is selected from the formulae (A-1) to (A-20)

wherein R 2 in formulae (A-17) to (A-20), is identically or differently H, alkyl groups having 1 to 20 C atoms, or phenyl.

3. The compound according to claim 2 , wherein
the group Ar* conforms to the following formula (H) and
Y is O or S;
p is 1; and
the group Ar* is connected to the group L at any position.

4. The compound according to claim 3 , wherein
R 1 is identically or differently, H, D, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 3 , or an aromatic ring system having 6 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , and
R 3 is on each occurrence, identically or differently, H, D, F, CN, Si(R 4 ) 3 or a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 4 , or an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 ,
R 4 is on each occurrence, identically or differently, 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 may be replaced by D or F.

5. The compound according to claim 1 , wherein the bonding position of the group L-Ar* to the aromatic six-membered ring of the basic structure of the formula (1-A-1) or formula (1-A-2) is in the para- or meta-position to the nitrogen atom.

6. The compound according to claim 1 , wherein the groups R 1 of the group C(R 1 ) 2 , do not represent an aromatic ring system and do not represent an aryl group.

7. The compound according to claim 1 , wherein the compound contains no electron-deficient heteroaryl group and no keto group, no phosphorus oxide group and no sulfur oxide group.

8. A process for the preparation of the compound according to claim 1 , which comprises one or more transition metal-catalysed, coupling reactions by means of which aryl or heteroaryl groups are introduced as substituents are carried out starting from a dihydroacridine derivative.

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

10. A formulation comprising at least one polymer, ol

Assignees

• Montenegro Elvira
• Buesing Arne
• Voges Frank
• Pflumm Christof
• Merck Patent Gmbh

Inventors

• Montenegro Elvira
• Buesing Arne
• Voges Frank
• Pflumm Christof

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• C07D279/26

  without other substituents attached to the ring system · CPC title

• H01L51/0087

  Electricity · mapped topic