# US 9,040,512 B2 · Phosphorus-containing metal complexes

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- Number: US 9,040,512 B2
- Document ID: US9040512B2
- Status: Granted
- Kind: B2
- Application number: 13/825,654
- Filed: 2011-09-01
- Published: 2013-09-26
- Granted: 2015-05-26
- Earliest claimed: 2010-09-24
- Assignees: Merck Patent GmbH
- Applicants: Rémi Manouk Anémian; Burkhard Koenig; Claire de Nonancourt
- Inventors: Rémi Manouk Anémian; Burkhard Koenig; Claire de Nonancourt
- Web page: https://patentgrep.com/patent/US9040512B2

## CPC

- C09K 11/06: containing organic luminescent materials
- A61N 5/062: {Photodynamic therapy, i.e. excitation of an agent}
- C07F 15/0033: {Iridium compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- H10K 85/342: {comprising iridium}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/16: Electron transporting layers
- H10K 50/18: Carrier blocking layers
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 2101/10: Triplet emission
- H10K 2102/00: Constructional details relating to the organic devices covered by this subclass
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates, inter alia, to metal complexes having improved solubility, to processes for the preparaion of the metal complexes, to devices comprising these metal complexes and to the use of the metal complexes.

## Claims

### Claim 1

A compound of the formula (1)
M(L)n(L′)m formula (1)
where the compound contains a moiety M(L)n is selected from the formulae (36) to (59)
wherein
X is CR1;
R1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylakoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R2, or an aryloxy, arylalkoxy, alkylaryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a diarylamino group, diheteroarylamino group or aryiheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of two or more of these groups; two or more radicals R1 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
M is iridium or platinum;
L′ is, identically or differently on each occurrence, a co-ligand;
W is, identically or differently on each occurrence, a radical of the formulae (3) and (4)
where V is equal to S or O;
R4 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R2)2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R2, or an aryloxy, arylalkoxy, alkylaryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, 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 R2, or a combination of two or more of these groups; two or more radicals R4 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R3, where one or more non-adjacent CH2 groups is optionally replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R3, or an aryloxy, arylalkoxy, alkylaryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, 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 R3, or a combination of two or more of these groups; two or more adjacent radicals R2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R3 is, identically or differently on each occurrence, H, D, F 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 F; two or more substituents R3 here optionally also forms a mono- or polycyclic, aliphatic or aromatic ring system with one another;
n is 1, 2 or 3 for M equal to iridium and is 1 or 2 for M equal to platinum;
m is 0, 1, 2 for M equal to iridium and is 0 or 1 for M equal to platinum;
the indices n and m here are selected so that the coordination number on the metal corresponds to 6 for M equal to iridium or rhodium and corresponds to 4 for M equal to platinum or palladium.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the moiety M(L)n is selected from the formulae (36), (40), (44), (48), (52), and (56).

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the radical W is given by the formulae (110) to (115)
where
R5 is, identically or differently on each occurrence, H, D, a straight-chain alkyl or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, 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 R2, or a combination of two or more of these groups; two or more radicals R1 here optionally also forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein M is equal to iridium.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein m=0.

### Claim 6 (depends on 1)

A process for the preparation of the compound according to claim 1 which comprises reacting the corresponding free ligands with metal alkoxides of the formula (344), with metal ketoketonates of the formula (345) or with metal halides of the formula (346)
where the symbols M, n and R1 have the meanings indicated in claim 1 and Hal=F, Cl, Br or I.

### Claim 7 (depends on 1)

A formulation comprising at least one compound according to claim 1 and at least one solvent.