Metal complexes

Patent metadata

Field	Value
Publication number	US-9382253-B2
Application number	US-201113809905-A
Country	US
Kind code	B2
Filing date	Jun 17, 2011
Priority date	Jul 16, 2010
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

Abstract

The present invention relates to metal complexes which contain polymerizable groups and to the polymers obtained using these metal complexes and to electronic devices, in particular organic electroluminescent devices, comprising these polymers. The metal complexes are compounds of the formula (1), containing a moiety M(L)n of the formula (2) or formula (3).

First claim

The invention claimed is:

1. A compound of the formula (1),
M(L) n (L′) m   formula (1)

containing a moiety M(L) n of the formula (2) or formula (3):

where the following applies to the symbols and indices used:
M is a metal;
X is selected on each occurrence, identically or differently, from the group consisting of C and N; all X here together represent a 14 π electron system;
R 1 to R 7 is on each occurrence, identically or differently, a polymerisable group PG or 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, alkynyl or imine group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, where the above-mentioned alkyl, alkoxy, thioalkoxy, alkenyl, alkynyl and imine groups may each be 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 , Si(R 8 ) 2 , Ge(R 8 ) 2 , Sn(R 8 ) 2 , C═O, C═S, C═Se, 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, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally 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 1 and R 2 and/or R 2 and R 3 and/or R 4 and R 5 and/or R 5 and R 6 and/or R 6 and R 7 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another; furthermore, R 3 and R 4 may form a mono- or polycyclic, in each case aliphatic ring system with one another;
with the proviso that R 1 , R 2 , R 3 , R 4 , R 5 , R 6 or R 7 represents a free electron pair if the group X to which this radical R 1 , R 2 , R 3 , R 4 , R 5 , R 6 or R 7 is bonded is a nitrogen atom having 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 , Ge(R 9 ) 2 , Sn(R 9 ) 2 , C═O, C═S, C═Se, 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, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally 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 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 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, CN 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 D or F; two or more substituents R 9 here optionally forms a mono- or polycyclic, aliphatic or aromatic ring system with one another;
PG is a polymerisable group, with the proviso that the polymerisable group is not selected from Cl, Br, I and B(OR 8 ) 2 ; and furthermore with the proviso that, if one or more of the radicals R 1 to R 7 as polymerisable group PG are selected from an alkenyl or an alkynyl group, it is a terminal alkenyl or alkynyl group having 3 to 40 C atoms, where individual CH 2 groups or individual H atoms may also be replaced by the groups mentioned above in the case of R 1 to R 7 ; and furthermore with the proviso that, if one or more of the radicals R 1 to R 7 as polymerisable group PG is selected from a group Si(R 8 ) 3 , R 8 stands either for Cl or for an alkoxy group having 1 to 40 C atoms;
L′ is, identically or differently on each occurrence, a co-ligand;
n is 1, 2 or 3;
m is 0, 1, 2, 3 or 4;

a plurality of ligands L here may also be linked to one another or L is optionally linked to L′ via a single bond or a bridge V and thus form a tridentate, tetradentate, pentadentate or hexadentate ligand system;
wherein at least one of the radicals R 1 to R 7 and/or at least one radical on the ligand stands for a polymerisable group PG.

2. The compound according to claim 1 , wherein the moieties of the formula (2) are selected from the formula (2a) and the moieties of the formula (3) are selected from the formula (3a),

where symbols and indices used have the meanings given in claim 1 and furthermore:
X 1 is, identically or differently on each occurrence, C or N, with the proviso that at least one group X 1 stands for N.

3. The compound according to claim 1 , wherein the moieties of the formula (2) are selected from the formulae (4), (5) and (6) and the moieties of the formula (3) are selected from the formulae (7) and (8),

where the symbols and indices have the meanings indicated in claim 1 .

4. The compound according to claim 1 , wherein the moieties of the formula (2) or (3) are selected from the formulae (78) and (79),

where symbols and indices used have the meanings given in claim 1 and furthermore:
Y is, identically or differently on each occurrence, CR 8 or N, with the proviso that a maximum of two symbols Y stand for N; and
X 2 is, identically or differently on each occurrence, C or N, with the proviso that precisely two symbols X 2 stand for N and the other symbols X 2 stand for C.

5. The compound according to claim 1 , wherein the moieties of the formulae (78) and (79) are selected from the formulae (78a) to (78d) and (79a) to (79d),

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

6. The compound according to claim 1 , selected from the compounds of the formulae (94) to (101),

where symbols used

Assignees

• Stoessel Philipp
• Joosten Dominik
• Gerhard Anja
• Breuning Esther
• Schulte Niels
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Joosten Dominik
• Gerhard Anja
• Breuning Esther
• Schulte Niels

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• 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

• H01L51/0087

  Electricity · mapped topic

• C07C49/796

  polycyclic · CPC title

• H01L51/5016

  Electricity · mapped topic