Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9379330-B2
Application number	US-201113805927-A
Country	US
Kind code	B2
Filing date	May 30, 2011
Priority date	Jun 22, 2010
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

The present invention relates to an electronic device comprising anode, cathode and at least one organic layer which comprises a compound of the formula (I) to (IV). The invention furthermore encompasses the use of compounds of the formula (I) to (IV) in an electronic device and to a compound of the formula (Ic) to (IVc).

First claim

The invention claimed is:

1. An electronic device comprising anode, cathode and at least one organic layer, characterised in that the organic layer comprises at least one compound of the following formulae (I) or (III)

where the following applies to the symbols occurring:
X is on each occurrence, identically or differently, C═O, C═S, C═NR 1 , C(R 1 ) 2 , C(R 1 ) 2 —C(R 1 ) 2 , CR 1 ═CR 1 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, SO or SO 2 ;
L is a divalent, or in the case of k=3, 4, 5 or 6 a tri-, tetra-, penta- or hexavalent group respectively, selected from C═O, C═NR 1 , Si(R 1 ) 2 , P(═O)(R 1 ), SO, SO 2 , alkylene groups having 1 to 20 C atoms, alkenylene or alkynylene groups having 2 to 20 C atoms, where, in the case of the groups mentioned, one or more CH 2 groups is optionally replaced by Si(R 1 ) 2 , O, S, C═O, C═NR 1 , C═O—O, C═O—NR 1 , NR 1 , P(═O)(R 1 ), 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 , aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 1 , and any combinations of 1, 2, 3, 4 or 5 identical or different groups selected from the above-mentioned groups; or L is a single bond, where k in this case must be equal to 2;
R 0 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 1 , OSO 2 R 1 , COOR 1 , CON(R 1 ) 2 , a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 1 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , —O—, —S—, —COO— or —CONR 1 — 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 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or a combination of these systems, furthermore, two or more adjacent radicals R 0 is optionally linked to one another here and form an aliphatic or aromatic ring, or a radical R 0 is optionally linked to an adjacent radical R via a single bond or a divalent group Y and form an aliphatic or aromatic ring;
R is equal to C(═O)R 1 , OSO 2 R 1 , COOR 1 , CON(R 1 ) 2 , a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 1 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , —O—, —S—, —COO— or —CONR 1 — and where one or more II 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 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or a combination of these systems, where furthermore the radical R is optionally linked to one or more adjacent radicals R 0 via a single bond or a divalent group Y;
Y is on each occurrence, identically or differently, a divalent group selected from C═O, C═S, C═NR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, SO and SO 2 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , OH, COOR 2 , CON(R 2 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , —O—, —S—, —COO— or —CONR 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 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems, where two or more radicals R 1 is optionally linked to one another and may form an aliphatic or aromatic ring;
R 2 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/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 2 here may also be linked to one another and form an aliphatic or aromatic ring; and
k is equal to 2, 3, 4, 5 or 6.

2. The electronic device according to claim 1 , wherein the compound of one of the formulae (I) or (III) represents a compound of one of the formulae (Ia), (Ib), (IIIa) and (IIIb),

where the symbols occurring are as defined in claim 1 and furthermore:
Ar 1 and Ar 2 are, identically or differently, an aryl group containing 6 to 60 aromatic ring atoms or a heteroaryl group containing 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 1 ; and
R is optionally linked, analogously to the definition indicated in claim 1 , to one or more radicals R 0 and/or an adjacent group Ar 1 or Ar 2 via a single bond or via a divalent group Y.

3. The electronic device according to claim 1 , wherein that the compound of one of the formulae (I) or (III) represents a compound of one of the formulae (Ic) and (IIIc).

where the symbols occurring are as defined in claim 1 and furthermore:
Ar 1 and Ar 2 are, identically or differently, an aryl group containing 6 to 60 aromatic ring atoms or a heteroaryl group containing 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 1 ; and
R is optionally linked, analogously to the definition indicated in claim 1 , to one or more adjacent groups Ar 1 and Ar 2 via a single bond or via a divalent group Y.

4. The electronic device according to claim 1 , wherein X is selected from a single bond, C═O and C(R 1 ) 2 .

5. The electronic device according to claim 1 , wherein the radical R represents an aryl or heteroaryl group having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , or represents an aralkyl or heteroaralkyl group having 5 to 20 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , where the radical R may furthermore be linked to one of the groups Ar 1 and Ar 2 vi

Assignees

• Stoessel Philipp
• Buesing Arne
• Joosten Dominik
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Buesing Arne
• Joosten Dominik

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title