Polycyclic phenylpyridine iridium complexes and derivatives thereof for oleds

Patent metadata

Field	Value
Publication number	US-2016233444-A1
Application number	US-201415022231-A
Country	US
Kind code	A1
Filing date	Aug 19, 2014
Priority date	Sep 17, 2013
Publication date	Aug 11, 2016
Grant date	—

Abstract

The present invention relates to metal complexes for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these metal complexes, especially as emitters. The compounds claimed have the formula: M(L) n (L′) m formula (1), where the compound of the general formula (1) contains a substructure M(L) n of the formula (2) or formula (3), where A is the same or different at each instance and is a group of the formula (A) which follows. Also claimed are processes for preparing such compounds, one of which is shown by way of example (I).

First claim

1 - 15 . (canceled)

16 . A compound of formula (1):
M(L) n (L′) m   (1)

wherein the compound of formula (1) contains a substructure M(L) n of formula (2) or formula (3):

wherein A is the same or different in each instance and is a group of formula (A):

wherein the dotted bond in formula (A) denotes the position of the linkage of this group;
M is a metal selected from the group consisting of iridium, rhodium, platinum, and palladium;
X is the same or different in each instance and is CR 1 or N;
Q is the same or different in each instance and is R 1 C═CR 1 , R 1 C═N, O, S, Se, or NR 1 ;
V is the same or different in each instance and is O, S, Se, or NR 1 ;
Y is the same or different in each instance and is a single bond or a bivalent group selected from the group consisting of C(R 1 ) 2 , C(═O), O, S, NR 1 , and BR 1 ;
R 1 is the same or different in each instance and is H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 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 40 carbon atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R 2 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S, or CONR 2 and wherein one or more hydrogen atoms are 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 and is optionally substituted in each case by one or more R 2 radicals, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or a combination of two or more of these groups; and wherein two or more R 1 radicals together optionally define a mono- or polycyclic, aliphatic, aromatic and/or benzofused ring system;
R 2 is the same or different in each instance and is 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 40 carbon atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R 3 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S, or CONR 3 and wherein one or more hydrogen atoms are 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 and is optionally substituted by one or more R 3 radicals, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 3 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 3 radicals, or a combination of two or more of these groups; and wherein two or more adjacent R 2 radicals together optionally define a mono- or polycyclic, aliphatic, aromatic, and/or benzofused ring system;
R 3 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by F; and wherein two or more R 3 substituents together optionally define a mono- or polycyclic, aliphatic, aromatic, and/or benzofused ring system;
L′ is the same or different in each instance and is a co-ligand;
n is 1, 2, or 3 when M is iridium or rhodium and is 1 or 2 when M is platinum or palladium;
m is 0, 1, 2, 3, or 4;
a, b, and c
is the same or different in each instance and is 0 or 1, wherein when a is 0 or b is 0 or c is 0, the respective Y group is absent and, instead, an R 1 radical is bonded to the corresponding carbon atoms in each case, with the proviso that a+b+c≧2; and

wherein two or more ligands L are optionally joined to one another or L is optionally joined to L′ via any bridge Z, thus forming a tridentate, tetradentate, pentadentate, or hexadentate ligand system.

17 . The compound of claim 16 , wherein zero or one X per cycle is N and the other X are CR 1 .

18 . The compound of claim 16 , wherein in the group of formula (A), two of the indices a, b, and c is 1 and the third is 0.

19 . The compound of claim 16 , wherein the group of formula (A) is the same or different in each instance and is selected from the group consisting of formulae (A-1), (A-2), and (A-3):

wherein Y is C(R 1 ) 2 , NR 1 , O, or S.

20 . The compound of claim 19 , wherein X is CR 1 .

21 . The compound of claim 16 , wherein the group of formula (A) is the same or different in each instance and is selected from the group consisting of formulae (A-1b), (A-2b), and (A-3b):

22 . The compound of claim 19 , wherein:
M is iridium or platinum; X is the same or different in each instance and is CR 1 ; Q is the same or different in each instance and is R 1 C═CR 1 or R 1 C═N; V is the same or different in each instance and is O, S, or NR 1 ; and Y is the same or different in each instance and is C(R 1 ) 2 , NR 1 , or O.

23 . The compound of claim 21 , wherein:
M is iridium; X is the same or different at each instance and is CR 1 ; Q is the same or different at each instance and is R 1 C═CR 1 ; V is S; and Y is the same or different at each instance and is C(R 1 ) 2 , NR 1 , or O.

24 . The compound of claim 16 , wherein adjacent R 1 radicals together define a ring, wherein the substructures of formulae (2) or (3) are selected from the group consisting of substructures of formulae (4-1), (4-2), (4-3), (4-4), (5-1), (5-2), and (5-3):

25 . The compound of claim 16 , wherein rather than one of the R 1 radicals, a bridging Z unit is present, and the compounds are selected from the group consisting of groups of formulae (6) to (9):

wherein Z is a bridging unit containing 1 to 80 atoms from the third, fourth, fifth, and/or sixth main groups or a 3- to 6-membered homo- or heterocycle which covalently bonds the sub-ligands L to one another or L to L′.

26 . The compound of claim 16 , wherein L′ is selected from the group consisting of carbon monoxide, nitrogen monoxide, alkyl cyanides, aryl cyanides, alkyl isocyanides, aryl isocyanides, amines, phos

Assignees

• Merck Patent Gmbh

Inventors

• Hayer Anna
• Joosten Dominik
• Heil Holger
• Anémian Rémi Manouk
• Nonancourt Claire

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/185

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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1033

  with oxygen · CPC title