# US 10,308,767 B2 · Alkoxysilane-modified polyamic acid solution, laminate and flexible device using same, and laminate manufacturing method

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- Number: US 10,308,767 B2
- Document ID: US10308767B2
- Status: Granted
- Kind: B2
- Application number: 15/502,706
- Filed: 2015-07-15
- Published: 2017-08-17
- Granted: 2019-06-04
- Earliest claimed: 2014-08-12
- Assignees: Kaneka Corporation
- Applicants: Kaneka Corporation
- Inventors: Takahiro Akinaga; Yuki Takiguchi; Shinji Ozawa
- Web page: https://patentgrep.com/patent/US10308767B2

## CPC

- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- B32B 27/281: {comprising polyimides}
- B32B 27/34: comprising polyamides
- C08G 73/1017: {in the form of (mono)amine}
- C08G 73/1028: {characterised by the process itself, e.g. steps, continuous}
- C08G 73/1032: {characterised by the solvent(s) used}
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- H05K 1/0326: {containing O}
- H05K 1/0346: {containing N}
- H05K 1/036: {Multilayers with layers of different types}
- H05K 1/0393: {Flexible materials (H05K1/038 takes precedence; specific organic compositions are classified in H05K1/0313 and subgroups)}
- H05K 3/0011: {Working of insulating substrates or insulating layers}
- H05K 3/007: {Manufacture or processing of a substrate for a printed circuit board supported by a temporary or sacrificial carrier (H05K1/187, H05K3/20 and H05K3/4682 take precedence)}
- B32B 2457/00: Electrical equipment
- H05K 1/0306: {Inorganic insulating substrates, e.g. ceramic, glass}
- H05K 2201/0154: Polyimide
- H05K 2201/0162: Silicon containing polymer, e.g. silicone
- H05K 2203/0264: Peeling insulating layer, e.g. foil, or separating mask
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS

## Abstract

Provided are a polyamic acid solution that can be formed into a film without peeling even when the film is thick and can be stably stored at room temperature, and a laminate that can be suitably used for production of a flexible device. In the alkoxysilane-modified polyamic acid solution according to the present invention, an additive amount of an alkoxysilane compound that contains an amino group is more than 0.050 parts by weight and less than 0.100 parts by weight.

## Claims

### Claim 1

An alkoxysilane-modified polyamic acid solution obtained by reacting an alkoxysilane compound and a polyamic acid in a solution with stirring at 50° C. to 80° C. for 2 to 5 hours, wherein the alkoxysilane compound comprises an amino group,
wherein
the polyamic acid is obtained by reacting an aromatic diamine and an aromatic tetracarboxylic acid dianhydride in a solvent,
a molar ratio obtained by dividing a total number of moles of the aromatic tetracarboxylic acid dianhydride by a total number of moles of the aromatic diamine is 0.980 or more and 0.9995 or less, and,
when an amount of the polyamic acid contained in the alkoxysilane-modified polyamic acid solution is 100 parts by weight, an additive amount of the alkoxysilane compound is more than 0.050 parts by weight and less than 0.100 parts by weight.

### Claim 2 (depends on 1)

The alkoxysilane-modified polyamic acid solution according to claim 1, wherein
the aromatic tetracarboxylic acid dianhydride is 3,3′,4,4′-biphenyl-tetracarboxylic acid dianhydride, and
the aromatic diamine is an aromatic diamine represented by the following Formula (1):
wherein n is an integer of 1 to 3.

### Claim 3 (depends on 1)

The alkoxysilane-modified polyamic acid solution according to claim 1, wherein a main component of the solvent is an amide solvent.

### Claim 4 (depends on 1)

A flexible device comprising:
a polyimide film obtained from the alkoxysilane-modified polyamic acid solution according to claim 1; and
an electronic element formed on the polyimide film.

### Claim 5 (depends on 1)

A laminate manufacturing method comprising:
obtaining a laminate by laminating a polyimide film on an inorganic substrate,
wherein the polyimide film is obtained from the alkoxysilane-modified polyamic acid solution according to claim 1 by casting and thermally imidizing the alkoxysilane-modified polyamic acid solution on the inorganic substrate.

### Claim 6 (depends on 5)

A flexible device manufacturing method comprising:
forming an electronic element on a polyimide film of a laminate obtained using the laminate manufacturing method according to claim 5; and
peeling the polyimide film, on which the electronic element is formed, from an inorganic substrate of the laminate.

### Claim 7 (depends on 1)

A laminate comprising:
a polyimide film that is obtained from the alkoxysilane-modified polyamic acid solution according to claim 1; and
an inorganic substrate on which the polyimide film is laminated,
wherein the polyimide film has a linear expansion coefficient of from 1 to 10 ppm/° C.

### Claim 8 (depends on 7)

The laminate according to claim 7,
wherein
the inorganic substrate has a thickness of from 0.4 to 5.0 mm, and
the polyimide film has a thickness of from 10 to 50 μm.

### Claim 9

An alkoxysilane-modified polyamic acid solution obtained by reacting an alkoxysilane compound and a polyamic acid in a solution with stirring at 50° C. to 80° C. for 2 to 5 hours, wherein the alkoxysilane compound comprises an amino group,
wherein the polyamic acid is obtained by reacting an aromatic diamine and an aromatic tetracarboxylic acid dianhydride in a solvent,
wherein a molar ratio obtained by dividing a total number of moles of the aromatic tetracarboxylic acid dianhydride by a total number of moles of the aromatic diamine is 0.980 or more and 0.9995 or less,
wherein, when an amount of the polyamic acid contained in the alkoxysilane-modified polyamic acid solution is 100 parts by weight, an additive amount of the alkoxysilane compound is more than 0.050 parts by weight and less than 0.100 parts by weight, and
wherein a water content of the alkoxysilane-modified polyamic acid solution is 500 ppm or more and 3000 ppm or less.

### Claim 10

A method of manufacturing an alkoxysilane-modified polyamic acid solution, the method comprising:
obtaining a polyamic acid by reacting an aromatic diamine and an aromatic tetracarboxylic acid dianhydride in a solvent; and
obtaining an alkoxysilane-modified polyamic acid solution by reacting an alkoxysilane compound and the polyamic acid in a solution with stirring at 50° C. to 80° C. for 2 to 5 hours, wherein the alkoxysilane compound comprises an amino group,
wherein
a molar ratio obtained by dividing a total number of moles of the aromatic tetracarboxylic acid dianhydride by a total number of moles of the aromatic diamine is 0.980 or more and 0.9995 or less, and,
when an amount of the polyamic acid contained in the alkoxysilane-modified polyamic acid solution is 100 parts by weight, an additive amount of the alkoxysilane compound is more than 0.050 parts by weight and less than 0.100 parts by weight.

### Claim 11

A method of manufacturing an alkoxysilane-modified polyamic acid solution, the method comprising:
obtaining a polyamic acid by reacting an aromatic diamine and an aromatic tetracarboxylic acid dianhydride in a solvent; and
obtaining an alkoxysilane-modified polyamic acid solution by reacting an alkoxysilane compound and the polyamic acid in a solution with stirring at 50° C. to 80° C. for 2 to 5 hours, wherein the alkoxysilane compound comprises an amino group,
wherein a molar ratio obtained by dividing a total number of moles of the aromatic tetracarboxylic acid dianhydride by a total number of moles of the aromatic diamine is 0.980 or more and 0.9995 or less,
wherein, when an amount of the polyamic acid contained in the alkoxysilane-modified polyamic acid solution is 100 parts by weight, an additive amount of the alkoxysilane compound is more than 0.050 parts by weight and less than 0.100 parts by weight, and
wherein a water content of the alkoxysilane-modified polyamic acid solution is 500 ppm or more and 3000 ppm or less.