US 7,842,830 B2Granted

Transition-metal charge-transport materials, methods of fabrication thereof, and methods of use thereof

AssigneeGeorgia Tech Research Corporation

InventorsSeth Marder, Jian-Yang Cho, Bernard Kippelen, Benoit Domercq, Steve Barlow

Life of this patent

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Abstract

Briefly described, embodiments of this disclosure include transition-metal charge-transport materials, methods of forming transition-metal charge-transport materials, and methods of using the transition-metal charge-transport materials.

Claims20

Dependent claims

A charge-transport material, comprising:

a transition-metal charge-transport material monomer having a structure of Formula I:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

30 more elements

A charge-transport material, comprising:

a transition-metal charge-transport material monomer having a structure of Formula II:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

31 more elements

A polymer comprising a monomer selected from the group consisting of:

the Formula I monomer, the Formula II monomer, and a combination thereof;
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile, isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

64 more elements

A homopolymer comprising a monomer selected from the group consisting of:

the Formula I monomer, the Formula II monomer, and a combination thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile, isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

64 more elements

A copolymer comprising a monomer selected from the group consisting of:

the Formula I monomer, the Formula II monomer, and a combination thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile, isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

63 more elements

A device, comprising:

a polymer including a compound selected from the group consisting of:
the Formula I monomer, the Formula II monomer claim, and a combination thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile, isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

65 more elements

A polymer layer, comprising:

a plurality of layers, wherein each layer includes a monomer having a central aromatic core, wherein the central aromatic cores in the layers are stacked substantially over one another to form a one-dimensional charge transport column along the stacked central aromatic cores, wherein the monomer includes a compound selected from the group consisting of:
the Formula I monomer, the Formula II monomer, and a combination thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer haying a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile, isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

64 more elements

A device, comprising:

a first electrode;
a hole-transport layer disposed adjacent the first electrode;
an electron-transport layer disposed adjacent the hole-transport layer, and wherein the electron-transport material is selected from the group consisting of:
the Formula I monomer, the Formula II monomer, and a combination thereof;
and
a second electrode disposed adjacent the electron-transport layer,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styrol;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacrovl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III):
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

71 more elements

An organic photovoltaic cell comprised of:

a first electrode;
a hole-transport layer disposed adjacent the first electrode;
an electron-transport layer disposed adjacent the hole-transport layer, and wherein the electron-transport material is selected from the group consisting of:
the Formula I monomer, the Formula II monomer, and a combination thereof;
an exciton blocking layer disposed adjacent the electron-transport layer;
and
a second electrode disposed adjacent the exciton blocking layer,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons:
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

72 more elements

An organic field-effect transistor comprised of:

a substrate;
a gate electrode disposed on a first side of the substrate;
a gate insulator disposed on a second side of the substrate;
a source electrode disposed on a first portion of the gate insulator;
a drain electrode disposed on a second portion of the gate insulator;
and .
an electron-transport layer disposed on a third portion of the gate insulator, the source electrode, and the drain electrode, and wherein the electron-transport material is selected from the group consisting of:
the Formula I monomer, the Formula II monomer, and a combination thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver(III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl:
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

73 more elements

A material, comprising:

a mixture of components comprising a monomer, a polymer including the monomer, a co-polymer including the monomer, a homopolymer including the monomer, and combinations thereof;
wherein the monomer is selected from the group consisting of:
the Formula I monomer, the Formula II monomer, and a combination thereof;
wherein an amount of each monomer present in the mixture is selected to control at least one property of the mixture;
wherein the property is selected from one of:
volatility, solubility, crystallinity, melting point, phase transitions, shelf life, charge transport ability, and combinations thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer haying a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons:
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z″, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide:
a strained rinq olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

71 more elements

A material, comprising:

a mixture of components comprising a compound selected from the group consisting of:
the Formula I monomer, the Formula II monomer, and a combination thereof;
wherein an amount of each compound present in the mixture is selected to control at least one property of the mixture;
wherein the property is selected from one of:
volatility, solubility, crystallinity, melting point, phase transitions, shelf life, charge transport ability, and combinations thereof,
wherein Formula I monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I) rhodium (I), copper (II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of a halogen, NR3, PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons:
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from a polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from a group consisting of:
vinyl;
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate;
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:
and
wherein Formula II monomer having a structure:
wherein M is selected from the group consisting of:
nickel (II), palladium (II), platinum (II), cobalt (I), iridium (I), rhodium (I), copper(II), copper (III), silver (III), and gold (III);
wherein L and L′ are each independently selected from the group consisting of:
a halogen, NR3,PR3, NCS, SCN, and CN;
wherein R is selected from the group consisting of:
a linear or branched, unsubstituted alkyl group with up to 25 carbons;
a linear or branched, substituted alkyl group with up to 25 carbons;
an unsubstituted aryl group;
a substituted aryl group;
and when L is PR3, R is an alkoxy group (R′O);
wherein X and X′ are each independently selected from the group consisting of:
S, Se, O, NR′, and a combination thereof;
and
wherein Z, Z′, Z″ and Z′″ are each independently selected from polymerizable group,
wherein is R′ is selected from a polymerizable group;
wherein the polymerizable group is selected from the group consisting of:
vinyl:
allyl;
4-styryl;
acroyl;
epoxide;
oxetane;
cyclic-carbonate;
methacroyl;
acrylonitrile;
isocyanate;
isothiocyanate:
an epoxide;
a strained ring olefin;
(—CH2)ηSiCl3;
(—CH2)ηSi(OCH2CH3)3;
(—CH2)ηSi(OCH3)3, where η is an integer number from 0 to 25;
and a compound having the following structure:

70 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/629,268Filed 14 Jun 2005 · us provisional application
Priority: 14 Jun 2004
Published: US 2008/0121870 A129 May 2008
Granted: 30 Nov 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07C 325/04
Thioaldehydes; Thioketones; Thioquinones; Oxides thereof: thioquinones; Oxides thereof
C07C 325/02
Thioaldehydes; Thioketones; Thioquinones; Oxides thereof: thioketones; Oxides thereof
H10K 85/111
Organic polymers or oligomers: comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
H10K 85/30
Organic materials used in the body or electrodes of devices covered by this subclass: coordination compounds

Family

Application60/579,376Us provisional application · filed 14 Jun 2004
US 2008/0121870 A1Pre-grant publication · published 29 May 2008
US 7,842,830 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

11/629,268Filed 14 Jun 2005 · us provisional application

Priority

14 Jun 2004

Published

US 2008/0121870 A129 May 2008

Granted

30 Nov 2010

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07C 325/04
Thioaldehydes; Thioketones; Thioquinones; Oxides thereof: thioquinones; Oxides thereof
C07C 325/02
Thioaldehydes; Thioketones; Thioquinones; Oxides thereof: thioketones; Oxides thereof
H10K 85/111
Organic polymers or oligomers: comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
H10K 85/30
Organic materials used in the body or electrodes of devices covered by this subclass: coordination compounds