Metal complexes

Patent metadata

Field	Value
Publication number	US-10103340-B2
Application number	US-201214122844-A
Country	US
Kind code	B2
Filing date	May 10, 2012
Priority date	Jun 3, 2011
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The present invention relates to a compound of the formula (1),

a process to prepare the compound of formula (1), a formulation containing the compound of formula (1) and an electronic device containing the compound of formula (1).

First claim

The invention claimed is:

1. A compound of the formula (1),

where the following applies to the symbols used:
M is a transition metal;
A is N, P, B, C − or CR;
Y is on each occurrence, identically or differently, CR 2 , NR, O S or a single bond, where a maximum of one group Y stands for a single bond;
Z is on each occurrence, identically or differently, C or N, with the proviso that both Z stand for C if Ar 3 stands for an aromatic or heteroaromatic six-membered ring, and that either both Z stand for C or one Z stands for C and the other Z stands for N if Ar 3 stands for a heteroaromatic five-membered ring;
D is on each occurrence, identically or differently, C or N;
Ar 1 is on each occurrence, identically or differently, together with the group D and the three carbon atoms explicitly drawn in, one carbon bonded to Y, one carbon bonded to A and one carbon bonded to Ar 2 , an aryl or heteroaryl group having 5 to 13 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ;
Ar 2 is on each occurrence, identically or differently, together with the group D and the carbon atom explicitly drawn in, and bonded to Ar 1 , an aryl or heteroaryl group having 5 to 13 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ;
Ar 3 is, together with the two groups Z and the carbon atom, an aryl or heteroaryl group having 5 to 10 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ;
R and R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , OH, COOH, C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, or an aromatic or hetero-aromatic 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 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , 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 2 ; two adjacent radicals R or two adjacent radicals R 1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; furthermore, the radicals R 1 which are bonded to adjacent groups Ar 1 and Ar 2 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , C═O, NR 3 , O, S or CONR 3 and where one or more H atoms 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 3 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , 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 3 ;
R 3 is on each occurrence, identically or differently, H, D, F or an aliphatic or aromatic 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 3 here may also form a mono- or polycyclic, aliphatic ring system with one another.

2. The compound according to claim 1 , wherein M is selected from the group consisting of platinum, palladium, nickel, rhodium, iridium and gold.

3. The compound according to claim 1 , wherein two groups D stand for N and the other two groups D stand for C.

4. The compound according to claim 1 , wherein Y stands, identically or differently on each occurrence, for CR 2 or for a single bond, where a maximum of one group Y stands for a single bond.

5. The compound according to claim 1 , wherein the two bridges Y are selected identically.

6. A compound according to claim 1 of the formula (2),

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

7. The compound according to claim 1 , wherein Ar 3 is selected from the structures of the formulae (3), (4) and (5),

where X stands, identically or differently on each occurrence, for CR 1 or N or where two adjacent groups X in formula (3) together stand for NR, O or S and the other group X stands for CR 1 or N; * indicates the bond to Y, and # indicates the bond to A.

8. The compound according to claim 1 , wherein Ar 1 is selected, identically or differently on each occurrence, from the structures of the formulae (6) to (9), (11) and (14),

where the bond to A, Y, M and Ar 2 is in each case indicated by the dashed bonds, X stands on each occurrence, identically or differently, for CR 1 or N, V stands on each occurrence, identically or differently, for O, S or NR 1 and R 1 has the same meaning as described in claim 1 .

9. The compound according to claim 1 , wherein Ar 2 is selected, identically or differently on each occurrence, from the structures of the formulae (17)-(24), (27)-(33) and (35)-(38),

where the bond to M and Ar 1 is in each case indicated by the dashed bonds, X stands on each occurrence, identically or differently, for CR 1 or N, V stands on each occurrence, identically or differently, for O, S or NR 1 and R 1 has the same meaning as described in claim 1 .

10. The compound according to claim 1 , wherein R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Br, I, N(R 2 ) 2 , CN, Si(R 2 ) 3 , B(OR 2 )

Assignees

• Stoessel Philipp
• Breuning Esther
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Breuning Esther

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• H01L2251/5384

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H01L51/0087 Primary

  Electricity · mapped topic

• C07F1/12

  Gold compounds · CPC title