Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-9768385-B2
Application number	US-201214111237-A
Country	US
Kind code	B2
Filing date	Mar 15, 2012
Priority date	Apr 13, 2011
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

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

First claim

The invention claimed is:

1. A compound of formula (I) or (II)

wherein:
Y is selected on each occurrence, identically or differently, from BR 1 , C(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , C═S, Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, S═O and S(═O) 2 ;
L is selected from C═O, C═NR 1 , Si(R 1 ) 2 , NR 1 , P(═O)(R 1 ), O, S, SO, SO 2 , alkylene groups having 1 to 20 C atoms or alkenylene or alkynylene groups having 2 to 20 C atoms, where one or more CH 2 groups in the said groups may be 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 said groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , and aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , and any desired 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 p in this case must be equal to 2;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O) OR 2 , C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , N(R 2 ) 2 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , 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 2 and where one or more adjacent or non-adjacent CH 2 groups in the above-mentioned groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , —C(═O)O —, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups may be 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 may be substituted by one or more radicals R 2 ;
R 2 is on each occurrence, identically or differently, 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 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 adjacent or non-adjacent CH 2 groups in the above-mentioned groups may be replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, 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 may be 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 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may 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 or a ring system;
R 3 is on each occurrence, identically or differently, 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 may be replaced by D or F;
two or more substituents R 3 here may also be linked to one another and form a ring or a ring system;

n is equal to 0 or 1; and
p is equal to 2, 3, 4, 5 or 6;
where a benzene ring may optionally be condensed on at the positions marked by *, and
where the group Y and the nitrogen atom are bonded to the six-membered ring of the carbazole derivative in vicinal positions, and
where, in the formulae (I) and (II), furthermore no or 1, 2, 3, 4, 5 or 6 carbon atoms which are constituents of an aromatic or heteroaromatic ring may be replaced by N, and
where furthermore the compound of the formula (I) or (II) may be substituted by a radical R 1 at one or more positions depicted as unsubstituted; and
where, in formula (II), the moieties in square brackets which are bonded to L may be identical or different; and
where, in formula (II), the group L may be bonded at any desired position of the moiety in square brackets.

2. Compound according to claim 1 , characterised in that n is equal to zero.

3. Compound according to claim 1 , characterised in that p is equal to 2.

4. Compound according to claim 1 , characterised in that 0 or 1 carbon atom which is constituent of an aromatic or heteroaromatic ring in formula (I) or (II) has been replaced by N.

5. Compound according to claim 1 , characterised in that L is selected from a single bond, where p must be ═2, or from C═O, NR 1 , O, S, alkylene groups having 1 to 10 C atoms, alkenylene groups having 2 to 10 C atoms, where one or more CH 2 groups in the said groups may be replaced by C═O, NR 1 , P(═O)(R 1 ), O or S, and arylene or heteroarylene groups having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or from divalent aromatic or heteroaromatic ring systems of the formula (L-1)

where p is equal to 2 and furthermore:
Ar 1 is on each occurrence, identically or differently, 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 ;
E is on each occurrence, identically or differently, a single bond, C═O, NAr 1 , P(═O)(R 1 ), O, S, SO or SO 2 ;
i is on each occurrence, identically or differently, 0 or 1;
k,l are on each occurrence, identically or differently, 0, 1, 2 or 3, where the sum of the values of k and l must be greater than 0; and
where furthermore the groups Ar 1 may be connected to one another via one or more divalent groups T, where
T is selected on each occurrence, identically or differently, from a single bond, BR 1 , C(R 1 ) 2 , C═O, C═S, C═NR 1 , C═C(R 1 ) 2 , CR 1 ═CR 1 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, S═O and S(═O) 2 ; and
the symbols * mark bonds from the group L to the remainder of the compound.

6. Compound according to claim 1 , characterised in that Y is selected on each occurrence, identically or differently, from C(R 1 ) 2 , C═O, NR 1 , O and S.

7. Compound according to claim 1 , characterised in that the compound is selected from the following formulae

where no or 1, 2, 3, 4, 5 or 6 carbon atoms which are constituents of an aromatic or heteroaromatic ring in formula (I-1) to (I-27) may be replaced by N, and
where the compo

Assignees

• Pflumm Christof
• Martynova Irina
• Mujica-Fernaud Teresa
• Merck Patent Gmbh

Inventors

• Pflumm Christof
• Martynova Irina
• Mujica-Fernaud Teresa

Classifications

• C07D498/14

  Ortho-condensed systems · CPC title

• C09K2211/1051

  with sulfur · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D513/14

  Ortho-condensed systems · CPC title

• C09K2211/1048

  with oxygen · CPC title