# US 7,608,342 B2 · Photocurable, conductive, transparent polymer coatings

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- Number: US 7,608,342 B2
- Document ID: US7608342B2
- Status: Granted
- Kind: B2
- Application number: 11/550,279
- Filed: 2006-10-17
- Published: 2007-08-02
- Granted: 2009-10-27
- Earliest claimed: 2005-11-23
- Assignees: Brewer Science Inc.
- Inventors: Xing-Fu Zhong
- Web page: https://patentgrep.com/patent/US7608342B2

## CPC

- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof}
- Y10T 428/31507: Of polycarbonate
- Y10T 428/31645: Next to addition polymer from unsaturated monomers
- Y10T 428/31855: Of addition polymer from unsaturated monomers
- Y10T 428/31909: Next to second addition polymer from unsaturated monomers
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Photocurable, conductive, and transparent polymer coating compositions and methods of using the same are provided. The compositions include a photopolymer and an electrically conductive polymer dissolved or dispersed in a solvent system. Preferred photopolymers include water-miscible, multifunctional acrylates. Preferred electrically conductive polymers include poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonate) (PEDOT-PSS). The compositions preferably also contain a photoinitiator and may contain a water-immiscible acrylate and/or a surfactant. The compositions are applied to substrates and exposed to actinic radiation such as ultraviolet (UV) light to form a cured, durable, conductive, and transparent coating.

## Claims

### Claim 1

An electrically conductive composition comprising a photopolymer and an electrically conductive polymer dissolved or dispersed in a solvent system, said electrically conductive polymer comprising thiophene monomers, wherein a cured layer of said composition has a percent transmittance of at least about 80% when having a thickness of about 30 μm and at a light wavelength of about 500 nm.

### Claim 2 (depends on 1)

The composition of claim 1, wherein said electrically conductive polymer further includes monomers comprising sulfonate groups.

### Claim 3 (depends on 1)

The composition of claim 1, wherein said thiophene monomers comprise 3,4-ethylenedioxythiophene.

### Claim 4 (depends on 3)

The composition of claim 3, wherein said electrically conductive polymer comprises poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonate).

### Claim 5 (depends on 1)

The composition of claim 1, wherein said photopolymer is selected from the group consisting of acrylates, methacrylates, and mixtures thereof.

### Claim 6 (depends on 5)

The composition of claim 5, wherein said photopolymer is an acrylate including recurring monomers comprising a hydrophilic functional group and at least two groups selected from the group consisting of acryloyl groups, methacrylol groups, and mixtures thereof.

### Claim 7 (depends on 6)

The composition of claim 6, wherein said hydrophilic functional group is selected from the group consisting of ethylene oxides, carboxylic acids, and sulfonic acids.

### Claim 8 (depends on 6)

The composition of claim 6, wherein said acrylate is selected from the group consisting of poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, ethoxylated trimethyloipropane triacrylate, carboxylated urethane aclylate, and sulfonated urethane acrylate.

### Claim 9 (depends on 1)

The composition of claim 1, said composition further comprising a water-immiscible acrylate.

### Claim 10 (depends on 9)

The composition of claim 9, said water-immiscible acrylate being selected from the group consisting of pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, hexafunctional urethane acrylate, and mixtures thereof.

### Claim 11 (depends on 1)

The composition of claim 1, wherein said solvent system comprises a first solvent and a second solvent, each of said first and second solvents having respective boiling points that are less than about 5° C. apart.

### Claim 12 (depends on 11)

The composition of claim 11, wherein said first solvent is water and said second solvent is an organic solvent.

### Claim 13 (depends on 12)

The composition of claim 12, wherein said solvent system comprises from about 25-45% by weight water, based upon the total weight of the solvent system taken as 100% by weight.

### Claim 14 (depends on 12)

The composition of claim 12, wherein said second solvent is selected from the group consisting of 1-propanol, 2-butanol, and mixtures thereof.

### Claim 15 (depends on 1)

The composition of claim 1, said composition further comprising a photoinitiator.

### Claim 16 (depends on 1)

The composition of claim 1, said composition comprising less than about 1.1% by weight of said electrically conductive polymer, based upon the total weight of the solids in the composition taken as 100% by weight.

### Claim 17

A method of forming an electrically conductive coating, said method comprising the step of applying a composition to a substrate, said composition comprising a photopolymer and an electrically conductive polymer dissolved or dispersed in a solvent system, said electrically conductive polymer comprising thiophene monomers, wherein a cured layer of said composition has a percent transmittance of at least about 80% when having a thickness of about 30 μm and at a light wavelength of about 500 nm.

### Claim 18 (depends on 17)

The method of claim 17, wherein said substrate is selected from the group consisting of flat panel displays, polycarbonate substrates, plastic substrates, glass substrates, acrylic substrates, microelectronic substrates, optoelectronic substrates, aircraft windshields, aircraft canopies, automobile windshields, and automobile windows.

### Claim 19 (depends on 17)

The method of claim 17, wherein said composition further comprises a photoinitiator and further comprising the step of exposing said composition to light after said applying step.

### Claim 20 (depends on 19)

The method of claim 19, wherein said exposing step results in a cured layer of said composition.

### Claim 21 (depends on 19)

The method of claim 19, wherein said exposing step results in a cured layer of said composition, said cured layer having an electrical conductivity of at least about 10−7 S/cm.

### Claim 22 (depends on 19)

The method of claim 19, wherein said exposing step results in a cured layer of said composition, said cured layer having a hardness of at least about 7H.

### Claim 23 (depends on 17)

The method of claim 17, wherein said electrically conductive polymer further includes monomers comprising sulfonate groups.

### Claim 24 (depends on 17)

The method of claim 17, wherein said thiophene monomers comprise 3,4-ethylenedioxythiophene.

### Claim 25 (depends on 24)

The method of claim 24, wherein said electrically conductive polymer comprises poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonate).

### Claim 26 (depends on 17)

The method of claim 17, wherein said photopolymer is selected from the group consisting of acrylates, methacrylates, and mixtures thereof.

### Claim 27 (depends on 26)

The method of claim 26, wherein said photopolymer is an acrylate including recurring monomers comprising a hydrophilic functional group and at least two groups selected from the group consisting of acryloyl groups, methacrylol groups, and mixtures thereof.

### Claim 28 (depends on 27)

The method of claim 27, wherein said hydrophilic functional group is selected from the group consisting of ethylene oxides, carboxylic acids, and sulfonic acids.

### Claim 29 (depends on 27)

The method of claim 27, wherein said acrylate is selected from the group consisting of poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, ethoxylated trimethyloipropane triacrylate, carboxylated urethane acrylate, and sulfonated urethane acrylate.

### Claim 30 (depends on 17)

The method of claim 17, said composition further comprising a water-immiscible acrylate.

### Claim 31 (depends on 30)

The method of claim 30, said water-immiscible acrylate being selected from the group consisting of pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentacrythritol pentaacrylate, dipentaerythritol hexaacrylate, hexafunctional urethane acrylate, and mixtures thereof.

### Claim 32 (depends on 17)

The method of claim 17, wherein said solvent system comprises a first solvent and a second solvent, each of said first and second solvents having respective boiling points that are less than about 5° C. apart.

### Claim 33 (depends on 32)

The method of claim 32, wherein said first solvent is water and said second solvent is an organic solvent.

### Claim 34 (depends on 33)

The method of claim 33, wherein said solvent system comprises from about 15-25% by weight water, based upon the total weight of the solvent system taken as 100% by weight.

### Claim 35 (depends on 33)

The method of claim 33, wherein said second solvent is selected from the group consisting of 1-propanol, 2-butanol, and mixtures thereof.

### Claim 36 (depends on 17)

The method of claim 17, said composition comprising less than about 1.1% by weight of said electrically conductive polymer, based upon the total weight of the solids in the composition taken as 100% by weight.

### Claim 37

The combination of substrate having a surface and a layer of a composition adjacent said substrate surface, said composition comprising a photopolymer and an electrically conductive polymer dissolved or dispersed in a solvent system, said electrically conductive polymer comprising thiophene monomers, wherein said layer has a percent transmittance of at least about 80% when having a thickness of about 30 μm and at a light wavelength of about 500 nm.

### Claim 38 (depends on 37)

The combination of claim 37, wherein said substrate is selected from the group consisting of flat panel displays, polycarbonate substrates, plastic substrates, glass substrates, acrylic substrates, microelectronic substrates, optoelectronic substrates, aircraft windshields, aircraft canopies, automobile windshields, and automobile windows.

### Claim 39 (depends on 37)

The combination of claim 37, said cured layer has an electrical conductivity of at least about 10−7 S/cm.

### Claim 40 (depends on 37)

The combination of claim 37, wherein said cured layer has a hardness of at least about 7H.

### Claim 41 (depends on 37)

The combination of claim 37, wherein said electrically conductive polymer further includes monomers comprising sulfonate groups.

### Claim 42 (depends on 37)

The combination of claim 37, wherein said thiophene monomers comprise 3,4-ethylenedioxythiophene.

### Claim 43 (depends on 42)

The combination of claim 42, wherein said electrically conductive polymer comprises poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonate).

### Claim 44 (depends on 37)

The combination of claim 37, wherein said photopolymer is selected from the group consisting of acrylates, methacrylates, and mixtures thereof.

### Claim 45 (depends on 44)

The combination of claim 44, wherein said photopolymer is an acrylate including recurring monomers comprising a hydrophilic functional group and at least two groups selected from the group consisting of acryloyl groups, methacrylol groups, and mixtures thereof.

### Claim 46 (depends on 45)

The combination of claim 45, wherein said hydrophilic functional group is selected from the group consisting of ethylene oxides, carboxylic acids, and sulfonic acids.

### Claim 47 (depends on 45)

The combination of claim 45, wherein said acrylate is selected from the group consisting of poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, ethoxylated trimethylolpropane triacrylate, carboxylated urethane acrylate, and sulfonated urethane acrylate.

### Claim 48 (depends on 37)

The combination of claim 37, said composition further comprising a water-immiscible acrylate.

### Claim 49 (depends on 48)

The combination of claim 48, said water-immiscible acrylate being selected from the group consisting of pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacryl ate, dipentaerythritol hexaacrylate, hexafunctional urethane acrylate, and mixtures thereof.

### Claim 50 (depends on 37)

The combination of claim 37, wherein said solvent system comprises a first solvent and a second solvent, each of said first and second solvents having respective boiling points that are less than about 5 C. apart.

### Claim 51 (depends on 50)

The combination of claim 50, wherein said first solvent is water and said second solvent is an organic solvent.

### Claim 52 (depends on 51)

The combination of claim 51, wherein said solvent system comprises from about 15-25% by weight water, based upon the total weight of the solvent system taken as 100% by weight.

### Claim 53 (depends on 51)

The combination of claim 51, wherein said second solvent is selected from the group consisting of 1-propanol, 2-butanol, and mixtures thereof.

### Claim 54 (depends on 37)

The combination of claim 37, said composition comprising less than about 1.1% by weight of said electrically conductive polymer, based upon the total weight of the solids in the composition taken as 100% by weight.

### Claim 55 (depends on 1)

The composition of claim 1, said composition comprising from about 0.3-0.7% by weight of said electrically conductive polymer, based upon the total weight of the solids in the composition taken as 100% by weight.

### Claim 56 (depends on 1)

The composition of claim 1, wherein said thiophene monomers arc present in said electrically conductive polymer at a level of at least about 30% by weight, based upon the total weight of the electrically conductive polymer taken as 100% by weight.