Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9741944-B2
Application number	US-201615193732-A
Country	US
Kind code	B2
Filing date	Jun 27, 2016
Priority date	Jan 29, 2010
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

The present invention relates to coordination compounds which are used in an electron-transport layer in electronic devices, to ligands, and to the use thereof for the preparation of metal complexes, to a layer, and to an electronic device which comprise the compounds according to the invention, and to a process for the preparation of the compounds according to the invention.

First claim

The invention claimed is:

1. A compound of the general formula (1) or (2),

where the symbols and indices used have the following meanings:
G is, identically or differently on each occurrence, a group of the following formula (a), (b) or (c):

Q is, identically or differently on each occurrence, a N or CR 3 ,
V is selected from the group consisting of O, S, N, CR 4 and NR 4 , with the proviso that, if V is equal to 0, S or NR 4 , R 3 represents a non-bonding electron pair;
the two dashed bonds in formula (a) and (b) mean that one of the bonds is a single covalent bond and the other is a double covalent bond;
R 1 is selected identically or differently on each occurrence, from the group defined for R 2 , R 3 or R 4 ; where one R 1 is not present, and the quinoline unit is bonded to Y 2 at this position;
R 2 , R 3 and R 4 are, identically or differently on each occurrence, a H, D, F, Cl, Br, I, CHO, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 5 ═CR 5 Ar 1 , CN, NO 2 , Si(R 5 ) 3 , B(OAr 1 ) 2 , B(OR 5 ) 2 , OSO 2 R 5 , OH, a saturated or unsaturated, straight-chain, branched or cyclic C 1-40 -alkyl group, C 1-40 -alkoxy group or C 1-40 -thioalkyl group, each of which is optionally substituted by one or more radicals R 5 , where one or more non-adjacent CH 2 groups is optionally replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 , and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 6 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 6 , and a combination of these systems; where one of the substituents R 2 , R 3 or R 4 is not present on the group G, and the group G is bonded to Y 1 at this position;
W is, identically or differently on each occurrence, an O, S or NR B , where R 8 is selected from the group defined for R 2 , R 3 or R 4 ;
Y 1 and Y 2 are each, independently of one another, either not present, so that the groups bonded thereto are linked directly to one another by a single covalent bond, or are a saturated, linear, branched or cyclic C 1-40 -alkyl group or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which is optionally substituted by one or more radicals R 6 ;
Ar is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 9 , where R 9 is selected from the group defined for R 2 , R 3 or R 4 ;
Ar 1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 7 , where, in addition, two radicals Ar 1 which are bonded to the same nitrogen or phosphorus atom is optionally linked to one another by a single bond or a bridge selected from the group consisting of B(R 7 ), C(R 7 ) 2 , Si(R 7 ) 2 , C═O, C═NR 7 , C═C(R 7 ) 2 , O, S, S═O, SO 2 , N(R 7 ), P(R 7 ) and P(═O)R 7 ;
R 5 is, identically or differently on each occurrence, a H, D, a saturated or unsaturated, linear, branched or cyclic C 1-20 -alkyl group, in which one or more H atoms is optionally replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 20 ring atoms, in which one or more H atoms is optionally replaced by F, and which is optionally substituted by one or more radicals R 6 ;
R 6 is, identically or differently on each occurrence, a H, D, F, Cl, Br, I, CHO, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 7 ═CR 7 Ar 1 , CN, NO 2 , Si(R 7 ) 3 , B(OAr 1 ) 2 , B(OR 7 ) 2 , OSO 2 R 7 , OH, or a saturated or unsaturated, straight-chain, branched or cyclic C 1-40 -alkyl group, C 1-40 -alkoxy group or C 1-40 -thioalkyl group, each of which is optionally substituted by one or more radicals R 7 , where one or more non-adjacent CH 2 groups is optionally replaced by R 7 C═CR 7 , Si(R 7 ) 2 , Ge(R 7 ) 2 , Sn(R 7 ) 2 , C═O, C═S, C═Se, C═NR 7 , P(═O)(R 7 ), SO, SO 2 , NR 7 , O, S or CONR 7 , and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 ;
R 7 is identically or differently on each occurrence, a H, D, a saturated or unsaturated, linear, branched or cyclic C 1-20 -alkyl group, in which one or more H atoms is optionally replaced by F or D, and an aromatic or heteroaromatic ring system having 5 to 20 ring atoms, in which one or more H atoms is optionally replaced by F or D;
M is a metal or a metal ion selected from the group consisting of Mg, Zn, Be and Cu,
L′ is, identically or differently on each occurrence, a monodentate or bidentate ligand;
m is, identically or differently on each occurrence, 0, 1, 2, 3 or 4, with the proviso that at least one index m is >0;
n is 1, 2, 3 or 4;
r is 1, 2, 3 or 4;
k is, identically or differently on each occurrence, 0, 1, 2, 3, 4, 5 or 6; and
l is 0, 1, 2, 3, 4, 5 or 6.

2. The compound according to claim 1 , wherein the following applies to compounds of the formula (I):
if M is a metal having two coordination sites, then k is equal to 0;
if M is a metal having three coordination sites and L′ is a monodentate ligand, then k is equal to 1;
if M is a metal having four coordination sites and L′ is a monodentate ligand, then k is equal to 2;
if M is a metal having five coordination sites and L′ is a monodentate ligand, then k is equal to 3;
if M is a metal having six coordination sites and L′ is a monodentate ligand, then k is equal to 4;
if M is a metal having seven coordination sites and L′ is a monodentate ligand, then k is equal to 5;
if M is a metal having eight coordination sites and L′ is a monodentate ligand, then k is equal to 6;
if M is a metal having four coordination sites and L′ is a bidentate ligand, then k is equal to 1;
if M is a metal having six coordination sites and L′ is a bidentate ligand, then k is equal to 2;
if M is a metal having eight coordination sites and L′ is a bidentate ligand, then k is equal to 3;
and wherein the following applies to compounds of the formula (II):
if M is a metal having two coordination sites and r is equal to 1, then l is equal to 0;
if M is a metal having three coordination sites, L′ is a monodentate ligand and r is equal to 1, then l is equal to 1;
if M is a metal having four coordination sites, L′ is a monodentate ligand and r is equal to 1, then l is equal to 2;
if M is a metal having five coordination sites, L′ is a monodentate ligand and r is equal to 1, then l is equal to 3;
if M is a metal having six coordination sites, L′ is a monodentate ligand and r is equal to 1, then l is equal to 4;
if M is a metal having seven coordination sites, L′ is a monodentate ligand and r is equal to 1, then l is equal to 5;
if M is a metal having eight coordination sites, L′ is a monodentate ligand and r is equal to 1, then l is equal to 6;
if M is a metal having four coordination sites and r is equal to 2, then l is equal to 0;
if M is a metal having five coordination sites, L′ is a monodentate ligand and r is equal to 2, then l is equal to 1;
if M is a metal having six coordination sites, L′ is a monodentate ligand and r is equal to 2, then l is equal to 2;
if M is a metal having seven coordination sites, L′ is a monodentate ligand and r is equal to 2, the

Assignees

• Merck Patent Gmbh

Inventors

• Buesing Arne
• Heil Holger
• Mujica-Fernaud Teresa
• Martynova Irina

Classifications

• H01L51/0077 Primary

  Electricity · mapped topic

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• H01L51/5056

  Electricity · mapped topic

• C07F5/025

  Boronic and borinic acid compounds · CPC title