# US 9,040,710 B2 · Aryloxy-phthalocyanines of group IV metals

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- Number: US 9,040,710 B2
- Document ID: US9040710B2
- Status: Granted
- Kind: B2
- Application number: 14/197,903
- Filed: 2014-03-05
- Published: 2014-09-11
- Granted: 2015-05-26
- Earliest claimed: 2013-03-11
- Assignees: Saudi Basic Industries Corporation
- Applicants: Saudi Basic Industries Corporation
- Inventors: Timothy P. Bender; Benoit H. Lessard; Ahmed Abdelrahman; Amit Tevtia
- Web page: https://patentgrep.com/patent/US9040710B2

## CPC

- C07F 7/30: Germanium compounds
- C07F 7/025: {without C-silicon linkages}
- C07F 7/2284: {Compounds with one or more Sn-N linkages}
- H10K 85/311: {Phthalocyanine}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- 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 disclosure relates to a compound comprising an aryloxy-phthalocyanine compound of Group IV metals, a method for preparing aryloxy-phthalocyanine compound of Group IV metals and an article of manufacture made therefrom.

## Claims

### Claim 1

A compound of a general structure (I):
wherein M is silicon, tin, or a combination thereof;
wherein “n” is an integer equal to or greater than 0;
wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
wherein R2 is a meta-substituted aryl containing group having from about 7 to about 10 carbon atoms.

### Claim 2 (depends on 1)

The compound of claim 1, wherein n ranges from about 0 to about 4.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R2 has 7 carbon atoms.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R2 does not include a metal.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R2 does not include a heteroatom as a bridging group.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R2 further includes a halogen, wherein the halogen is fluorine, chlorine, bromine, iodine, or a combination thereof.

### Claim 7 (depends on 6)

The compound of claim 6, wherein R2 does not include chlorine.

### Claim 8 (depends on 6)

The compound of claim 6, wherein the halogen is chlorine.

### Claim 9 (depends on 6)

The compound of claim 6, wherein the halogen is chlorine at one or more ortho-positions of the aryl containing group.

### Claim 10

A compound of a general molecular structure (II):
wherein M is silicon, tin, or a combination thereof;
wherein “n” is an integer equal to or greater than 0;
wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof; and
wherein R2 and R3 are the same or different and are a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group and at least one or the R2 and R3 is a meta-substituted aryloxy containing group having from 7 to about 10 carbon atoms.

### Claim 11 (depends on 10)

The compound of claim 10, wherein n ranges from about 0 to about 4.

### Claim 12 (depends on 10)

The compound of claim 10, wherein the substituted aryloxy containing group has 7 carbon atoms.

### Claim 13 (depends on 10)

The compound of claim 10, wherein R2 and R3 do not include a metal.

### Claim 14 (depends on 10)

The compound of claim 10, wherein R2 and R3 do not include a heteroatom as a bridging group.

### Claim 15 (depends on 10)

The compound of claim 10, wherein R2 and R3includes a heteroatom, wherein the heteroatom is fluorine, chlorine, bromine, iodine, or a combination thereof.

### Claim 16 (depends on 15)

The compound of claim 15, wherein the halogen does not include chlorine.

### Claim 17 (depends on 15)

The compound of claim 15, wherein the halogen is chlorine, and wherein the aryloxy containing group is not substituted at a para-position. containing group, if substituted, cannot be substituted at a para-position.

### Claim 18 (depends on 15)

The compound of claim 15, wherein the halogen is chlorine, and wherein the aryloxy containing group is substituted at one or more ortho-positions.

### Claim 19

A method for preparing a compound of the general molecular structure (I):
wherein M is silicon, germanium, tin, or a combination thereof;
wherein “n”is an integer equal to or greater than 0;
wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
wherein R2 is a substituted aryl containing group having about 7 to about 22 carbon atoms, the method, comprising the steps of:
a) providing a compound having a halogen-metal bond containing R1 substituted phthalocyanines precursor, wherein the halogen is chlorine, bromine, iodine, fluorine, or a combination thereof; and wherein each R1 independently is a straight chain alkylgroup, a branched alkyl group, a cycloalkyl group, and alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
b) providing a reactant having a meta-substituted aryl (—R2 )or a meta-substituted arylalcohol group (OH—R2 ), wherein R2 comprises from 7 to about 22 carbon atoms, and
c)reacting the compound having a halogen-metal bond containing phthalocyanines precursor and the reactant in the presence of an organic solvent under conditions effective to form the compound of the general molecular structure (I), wherein the compound of the general molecular structure (I) is non-soluble, negiligibly soluble, partially soluble in an organic solvent, or at least partially soluble in an organic solvent.

### Claim 20 (depends on 19)

The method of claim 19, wherein R2has 7 carbon atoms.

### Claim 21 (depends on 19)

The method of claim 19, wherein the organic solvent is toluene, dimethylsulfoxide, or dichloromethane.

### Claim 22

A method for preparing a compound of the general molecular structure (II):
wherein M is silicon, germanium, -tin, or a combination thereof;
wherein “n”is an integer equal to or greater than 0;
wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof; and
wherein R2 and R3 are the sme or different and are a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group and at least one of the R2 and R3 is a substituted aryloxy containing group having about 7 to about 22 carbon atoms,
the method, comprising the steps of:
a) providing a compound having a halogen-metal bond containing R1 substituted phthalocyanines precursor, wherein the halogen is chlorine, bromine, iodine, fluorine, or a combination thereof, and wherein each R1 independently has a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, and alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydeogen, a halogen, or a combination thereof;
b) providing a reactant having R2 and/or R3 moieties, wherein R2 and R3 are the same or different and have a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group, and at least one of the R2 and R3 is aryloxy containing group having from 7 to about 10 carbon atoms; and
(c)reacting the compound having a halogen-metal bond containing phthalocyanines precursor and the reactant in the presence of an organic solvent under conditions effective to form the compound of the general molecular structure (II), wherein the compound of the general molecular structure (II) is non-soluble, negiligibly soluble, partially soluble in an organic solvent, or at least partially soluble in an organic solvent.

### Claim 23 (depends on 22)

The method of claim 22, wherein R2 and/or R3 moieties are added simultaneously or in a plurality of steps.

### Claim 24 (depends on 22)

The method of claim 22, wherein R2 and R3 are a meta-substituted aryloxy containing group having from 7 to about 10 carbon atoms.

### Claim 25 (depends on 22)

The method of claim 22, wherein the organic solvent is toluene, dimethylsulfoxide, dichloromethane, or a combination thereof.

### Claim 26 (depends on 1)

A photovoltaic cell comprising a compound having the general molecular structure (I)as claimed in claim 1.

### Claim 27 (depends on 10)

A photovoltaic cell comprising a compound having the general molecular structure (II)as claimed in claim 10.

### Claim 28 (depends on 1)

The compound of claim 1, wherein n is 1, and R2 is 3-methyly aryl.

### Claim 29 (depends on 10)

The compound of claim 10, wherein n is 1, R1 is hydrogen, and the aryloxy containing group is 3-methyl aryl.

### Claim 30 (depends on 10)

The compound of claim 10, wherein R2 and R3 are the same and the aryloxy containing groups are 3-methyl aryl.

### Claim 31 (depends on 19)

The method of claim 19, wherein n is 1, R1 is hydrogen, and R2 is 3-methyl aryl.

### Claim 32 (depends on 22)

The method of claim 22, wherein n is 1, R1 is hydrogen, and the aryloxy containing group is 3-methyl aryl.

### Claim 33 (depends on 22)

The method of claim 22, wherein n is 1, R2 and R3 are the same and the aryloxy containing groups are 3-methyl aryl.

### Claim 34

A compound of a general structure (I):
wherein M is silicon, germanium, tin, or a combination thereof;
wherein “n”is an integer equal to or greater than 0;
wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
wherein R2 is a substituted aryl containing group having about 7 to about 22 carbon atoms, and includes a halogen selected from the group consisting essentially of fluorine, chlorine, bromine, iodine, and a combination thereof.

### Claim 35

A compound of a general molecular structure (II):
wherein M is silicon, germanium, tin, or a combination thereof;
wherein “n”is an integer equal to or greater than 0;
wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof; and
wherein R2 and R3 are the same or different and are a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group and at least one of the R2 and R3 includes a substituted aryloxy containing group having about 7 to about 22 carbon atoms, and a halogen selected from the group consisting essentially of fluorine, chlorine, bromine, iodine, and a combination thereof.