Pt- or Pd-carbene complexes for use in organic light emitting diodes

Patent metadata

Field	Value
Publication number	US-10424746-B2
Application number	US-201515526787-A
Country	US
Kind code	B2
Filing date	Nov 18, 2015
Priority date	Nov 18, 2014
Publication date	Sep 24, 2019
Grant date	Sep 24, 2019

Abstract

The present invention relates to Pt- or Pd-amidine-carbene complexes, to organic light-emitting diodes (OLEDs) comprising at least one such Pt- or Pd-amidine-carbene complex, to light-emitting layers comprising at least one such Pt- or Pd-amidine-carbene complex, a device, for example stationary or mobile visual display units or illumination means, comprising a corresponding OLED, and to the use of the inventive Pt- or Pd-amidine-carbene complexes in OLEDs, for example as emitters, matrix materials, charge transport materials and/or charge blockers.

First claim

The invention claimed is:

1. A complex of the general formula (I) or (II)

wherein M, A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 10 are each defined as follows:
M is Pt or Pd,
A 1 is N or CR 8 ,
A 2 is N or CR 9 ,
R 1 and R 2
are independently of each other a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by at least one substituent E; a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR 65 and/or substituted by at least one substituent E; a C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR 65 ; a C 1 -C 18 haloalkyl group; or CN;
R 3
is hydrogen; a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by at least one substituent E; a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR 65 and/or substituted by at least one substituent E; a C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a —O—C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR 65 ; a halogen atom; a C 1 -C 18 haloalkyl group; or CN;
or
R 1 and R 3 or R 2 and R 3 together form a group of formula

wherein X′ is present in the position of R 3 and is selected from O, S, NR 75 and CR 73 R 74 ;
R f , R g , R h , R i , R j and R k are independently of each other H, a C 1 -C 5 alkyl group, a fluoroC 1 -C 4 alkyl group, or a C 3 -C 6 cycloalkyl group;
n is 0 or 1;

wherein the group of formula (III) comprises 0, 1 or 2 double bonds; in the case that 1 or 2 double bonds are present in the group of formula (III), the carbon atoms connected with the double bonds are each substituted by only one residue R f , R j and/or—in the case that n is 1—R h ;
R 5 and R 6
are independently of each other hydrogen; a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by at least one substituent E; a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR 65 and/or substituted by at least one substituent E; a C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a —NR 65 —C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR 65 ; a halogen atom; a C 1 -C 18 haloalkyl group; CN; or SiR 80 R 81 R 82 ; or
R 5 and R 6 together form a group of formula

wherein X is O, S, NR 75 or CR 73 R 74 ; R′″ is C 1 -C 8 alkyl and a is 0, 1 or 2;
R 4 and R 7
are independently of each other hydrogen; a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by at least one substituent E; a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR 65 and/or substituted by at least one substituent E; a C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR 65 a halogen atom; a C 1 -C 18 haloalkyl group; CN; or SiR 80 R 81 R 82 ;
or

R 6 and R 7 together form a group of formula

wherein X is O, S, NR 75 or CR 73 R 74 ; R′″ is C 1 -C 8 alkyl and a is 0, 1 or 2;
R 8 and R 9
are independently of each other hydrogen; a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by at least one substituent E; a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR 65 and/or substituted by at least one substituent E; a C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a —O—C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR 65 ; a halogen atom; a C 1 -C 18 haloalkyl group; or CN;
or
R 8 and R 9 together form a group of formula

wherein Y is N or CR n ; Z is N or CR o ;

R l , R m , R n and R o are independently of each other H, a C 1 -C 5 alkyl group, a fluoroC 1 -C 4 alkyl group, or a C 3 -C 6 cycloalkyl group;
R 10
is a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E; a C 3 -C 12 cycloalkyl group, which can optionally be substituted by at least one substituent E; a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR 65 and/or substituted by at least one substituent E; a C 6 -C 14 aryl group, which can optionally be substituted by at least one substituent G; a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR 65 ;
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C;
E is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, halogen, or a C 1 -C 18 alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D;
G is E; or an unsubstituted C 6 -C 14 aryl group; a C 6 -C 14 aryl group, which is substituted by F, C 1 -C 18 alkyl, or C 1 -C 18 alkyl, which is substituted by F and/or interrupted by O; an unsubstituted heteroaryl group comprising 5 to 11 ring atoms, interrupted by at least one of O, S, N and NR 65 ; or a heteroaryl group comprising 5 to 11 ring atoms, interrupted by at least one of O, S, N and NR 65 , which is substituted by F, unsubstituted C 1 -C 18 alkyl, SiR 80 R 81 R 82 , or C 1 -C 18 alkyl which is substituted by F and/or interrupted by O;
R 63 and R 64 are independently of each other H; unsubstituted C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; unsubstituted C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are independently of each other H, an unsubstituted C 6 -C 18 aryl group; a C 6 -C 18 aryl group which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; an u

Assignees

• Basf Se
• Udc Ireland Ltd

Inventors

• Metz Stefan
• Strassner Thomas
• Tronnier Alexander
• Tenne Mario

Classifications

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title