Platinum metal complexes with divalent groups bridging two ligands

Patent metadata

Field	Value
Publication number	US-9673402-B2
Application number	US-201214128654-A
Country	US
Kind code	B2
Filing date	May 30, 2012
Priority date	Jun 28, 2011
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

The present invention relates to metal complexes and to electronic devices, in particular organic electroluminescent devices, comprising these metal complexes.

First claim

The invention claimed is:

1. A compound of formula (1),

where L 1 stands, identically or differently on each occurrence, for a part-ligand of the following formula (2),

where the dashed bond indicates the bond to V, * denotes the position of the coordination to M and the following applies to the symbols and indices used:
M is Pt;
V is for NR 7 or O wherein when V is selected from NR 7 , L 1 and L 2 are directly bonded to N,
R 7 is of the formula (39) or (40)

where the dashed bond represents the bond to the nitrogen atom,
X is on each occurrence, identically or differently, C or N, where all X in the part-ligand of the formula (2) together form a 14π electron system, with the proviso that at least two groups X and at most 6 groups X in each part-ligand of the formula (2) stand for N;
R 1 to R 6 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 8 ) 2 , CN, NO 2 , Si(R 8 ) 3 , B(OR 8 ) 2 , C(═O)R 8 , P(═O)(R 8 ) 2 , S(═O)R 8 , S(═O) 2 R 8 , OSO 2 R 8 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 8 , where one or more non-adjacent CH 2 groups is optionally replaced by R 8 C═CR 8 ,C≡C, Si(R 8 ) 2 , C═O, C═S, C═NR 8 , P(═O)(R 8 ), SO, SO 2 , NR 8 , O, S or CONR 8 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, 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 8 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 8 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 8 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 8 ; R 4 and R 5 and/or R 5 and R 6 and/or R 1 and R 7 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another; furthermore, R 2 and R 3 may form a mono- or polycyclic, aliphatic ring system with one another; with the proviso that R 1 to R 6 represents a free electron pair if the group X to which this radical R 1 to R 6 is bonded is a nitrogen atom with a saturated valence;
R 8 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 9 ) 2 , CN, NO 2 , Si(R 9 ) 3 , B(OR 9 ) 2 , C(═O)R 9 , P(═O)(R 9 ) 2 , S(═O) R 9 , S(═O) 2 R 9 , OSO 2 R 9 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 9 , where one or more non-adjacent CH 2 groups is optionally replaced by R 9 C═CR 9 , C≡C, Si(R 9 ) 2 , C═O, C═S, C═NR 9 , P(═O)(R 9 ), SO, SO 2 , NR 9 , O, S or CONR 9 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, 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 9 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 9 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 9 , or a diarylamino group, diheteroarylarnino group or arylheleroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 9 ; two or more adjacent radicals R 8 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 9 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F; two or more substituents R 9 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
L 2 is a bidentate part-ligand which is bonded to V;
n is 1 or 2; and
m is (2−n).

2. The compound according to claim 1 , wherein the part-ligand of the formula (2) is selected from structures of the formula (4),

where the symbols used have the meanings given in claim 1 and at least one symbol X and at most 5 symbols X stand for N.

3. The compound according to claim 2 , wherein V is NR 7 and R 7 is of the formula (39).

4. The compound according to claim 2 , wherein V is NR 7 and R 7 is of the formula (40).

5. The compound according to claim 2 , wherein V is O.

6. The compound according to claim 1 , wherein the part-ligand of the formula (2) is selected from the part-ligands of the formulae (5), (6) or (7),

where the symbols used have the meanings given in claim 1 , in the case of the use of the part-ligands of the formula (7) the bridging unit V is selected from BR 7 and B(R 7 ) 2 and the part-ligands contain two, three, four, five or six nitrogen atoms.

7. The compound according to claim 1 , wherein the part-ligands of the formula (2) are selected from the part-ligands of the formulae (5a) to (5r), (6a) to (6r) or (7a) to (7r),

where the symbols used have the meanings given in claim 1 .

8. The compound according to claim 1 , wherein, if the part-ligand of the formula (2) contains 3 or more nitrogen atoms, a bulky radical which is selected, identically or differently on each occurrence, from the group consisting of N(R 8 ) 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 8 , where one or more non-adjacent CH 2 groups is optionally replaced by R 8 C═CR 8 , C≡C, Si(R

Assignees

• Stoessel Philipp
• Jatsch Anja
• Breuning Esther
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Jatsch Anja
• Breuning Esther

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

• C09K2211/185

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

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title