IP Library Granted Patent US 11,104,628
Granted Patent B2
US 11,104,628 · App. 16/499,478 · Granted Aug 31, 2021

Aromatic compounds

Inventors: Philipp Stoessel (Frankfurt am Main, DE); Christian Ehrenreich (Darmstadt, DE)
Assignee: Merck Patent GmbH
C07C25/18C07C17/35C07C25/22C07C41/18C07C43/225C07D213/06C07D213/127C07D239/30C07D401/14C07D405/14C07D471/04C07F7/081C07F7/083C07C2602/08C07C2602/10C07C2603/18
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Quick Facts
Patent No.
US 11,104,628
App. No.
16/499,478
Granted
Aug 31, 2021
Kind
B2
Abstract

The present invention relates to aromatic compounds suitable for preparation of asymmetric polydentate ligands. The present invention further describes a process for preparing asymmetric polydentate ligands and metal complexes comprising these ligands which are suitable for use as emitters in organic electroluminescent devices.

Claims (31)

1. A compound of formula (II):

wherein

Z a , Z b , and Z c

are the same or different and are Cl, Br, I, B(OR) 2 , OH, or OSO 2 R;

X is the same or different in each instance and is CR or N, or C if one R a , R b , or R c radical binds to X, with the proviso that not more than three X symbols per cycle are N;

R, R a , R b , and R c

are the same or different at each instance and are H, D, F, CN, Si(R 1 ) 3 a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group may be substituted by one or more R 1 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by Si(R 1 ) 2 , or O, or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and is optionally substituted in each case by one or more R 1 radicals; and wherein two R radicals together or together with one of the R a , R b , or R c radicals optionally defines a ring system;

R 1 is the same or different in each instance and is H, D, F, CN, Si(R 2 ) 3 , a straight-chain alkyl group having 1 to 10 carbon atoms or or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group is optionally substituted by one or more R 2 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by Si(R 2 ) 2 , or O, or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and is optionally substituted in each case by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 2 radicals; and wherein two or more R 1 radicals together optionally define a ring system; and

R 2 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic organic radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms is optionally replaced by F; and wherein two or more R 2 radicals together optionally define a ring system;

n is 0, 1, 2 or 3 and

wherein the compound of formula (I) does not have C 3 symmetry and wherein the Z a group is not the same as the Z b or Z c group.

2. The compound of claim 1 , wherein the R a group is not the same as the R b or R c group.

3. The compound of claim 1 , wherein the compound is a compound of formula (IV):

wherein n is the same or different in each instance and is 0, 1, 2, or 3.

4. The compound of claim 1 , wherein the Z a is not the same as the Z b group and the Z b group is not the same as the Z c group.

5. The compound of claim 1 , wherein the R a group is not the same as the R b group and the R c group, and the R b group is not the same as the R C group.

6. The compound of claim 1 , wherein at least one of the R a , R b , and R c groups is selected from a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein each alkyl alkenyl, or alkynyl group is optionally substituted by one or more R 1 radicals, wherein one or more nonadjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, NR 1 , O, S, or CONR 1 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms.

7. A process for preparing a polypodal ligand, comprising reacting a compound of claim 1 in a first step with a first reactive ligand in a coupling reaction to form product, reacting the product in a second step with a second reactive ligand in a coupling reaction, wherein the first and second reactive ligands are different, such that a bridge corresponding to the compound of claim 1 without the Z a , Z b , and Z c groups is formed between a sub-ligand derived from the first reactive ligand and a sub-ligand derived from the second reactive ligand.

8. The process of claim 7 , further comprising reacting the product obtained in the second step in a third step with a further reactive ligand in a coupling reaction, wherein the first, second and third reactive ligands are different.

9. The process of claim 7 , wherein at least one of the reactive ligands is a bidentate ligand of formula (L-1), (L-2), or (L-3):

wherein

CyC is the same or different in each instance and is an optionally substituted aryl or heteroaryl group which has 5 to 14 aromatic ring atoms and can coordinate in each case to a metal via a carbon atom and which is bonded in each case to CyD via a covalent bond; the optional substituents are selected from R;

CyD is the same or different in each instance and is an optionally substituted heteroaryl group which has 5 to 14 aromatic ring atoms and can coordinate to a metal via a nitrogen atom or via a carbene carbon atom and which is bonded to CyC via a covalent bond; and

Z d is a reactive group.

10. The compound of claim 1 , wherein R 2 is a hydrocarbyl radical.

11. The compound of claim 1 , wherein n is 0 or 1.

12. The compound of claim 6 , wherein at least one of the R a , R b , and R c groups is selected from a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl or alkynyl group having 2 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each alkyl alkenyl, or alkynyl group is optionally substituted by one or more R 1 radicals, wherein one or more nonadjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, NR 1 , O, S, or CONR 1 .

13. The process of claim 7 , wherein CyC and CyD are optionally substituted with one or more radicals R.

14. The process of claim 7 , wherein Z d is selected from the group consisting of Cl, Br, I, B(OR) 2 , OH, OSO 2 R, or an alkoxy or thioalkoxy group having 1 to 20 carbon atoms.

15. The compound of claim 1 , wherein at least one of the R a , R b , and R c groups is selected from a straight-chain alkyl group having 1 to 8 carbon atoms or a branched or cyclic alkyl group having 3 to 8 carbon atoms, wherein each alkyl group is optionally substituted by one or more R 1 radicals.

16. The compound of claim 1 , wherein W is identical or different and is H, F, CN, a straight-chain alkyl group having 1 to 5 carbon atoms or a branched or cyclic alkyl group having 3 to 5 carbon atoms, wherein each alkyl group is optionally substituted by one or more R 2 radicals or an aromatic or heteroaromatic ring system which has 5 to 13 aromatic ring atoms and is optionally substituted in each case by one or more R 2 radicals.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Feb 10, 2026
From: MERCK PATENT GMBH
To: UDC IRELAND LIMITED
Reel/Frame 073741/0073 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2020
From: STOESSEL, PHILIPP; EHRENREICH, CHRISTIAN
To: MERCK PATENT GMBH
Reel/Frame 052860/0124 →