# US 2013/0156960 A1 · Organic-inorgaic hybrid polyamic ester, method of fabricating the same, and method of fabricating a film thereof

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- Number: US 2013/0156960 A1
- Document ID: US20130156960A1
- Status: Published application
- Kind: A1
- Application number: 13/619,706
- Filed: 2012-09-14
- Published: 2013-06-20
- Earliest claimed: 2011-12-14
- Assignees: Electronics and Telecommunications Research Institute
- Inventors: Seung Koo PARK; Jeong Ik LEE; Doo-Hee CHO; Hye Yong CHU; Chul Woong JOO
- Web page: https://patentgrep.com/patent/US20130156960A1

## CPC

- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G 73/1039: {comprising halogen-containing substituents}
- C08G 73/1053: {with oxygen only in the tetracarboxylic moiety}
- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- C08G 73/1071: {Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain}
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

Provided are organic-inorganic hybrid polyamic ester, method of fabricating the same, and method of fabricating a film thereof. The polyamic ester is formed by chemically reacting an inorganic precursor containing inorganic and/or metal element with a polyamic acid having two carboxyl acid of good reactivity per a polymer repeating unit. The inorganic alkoxide is hydrolyzed to be the corresponding inorganic hydroxide. The hydroxyl group is reacted with the carboxylic acid of the polyamic acid and with the hydroxyl group of the other inorganic hydroxide. Therefore, the polyamic ester can steadily include more inorganic materials. The content amount of the inorganic material is relatively high, so that the polyamic ester may have superior refractive index, chemical and heat resistances.

## Claims

### Claim 1

Organic-inorganic hybrid polyamic ester comprising the following chemical formula 1,
wherein, in the chemical formula 1, the X is an alicyclic compound or an aromatic compound, the Y is at least one selected from a group consisting of an aliphatic compound, an alicyclic compound and an aromatic compound, and the I is at least one out of an inorganic element or a metal element.

### Claim 2 (depends on 1)

The organic-inorganic hybrid polyamic ester of claim 1, wherein the I is at least one selected from a group consisting of titanium oxide, silicon oxide and zirconium oxide.

### Claim 3 (depends on 1)

The organic-inorganic hybrid polyamic ester of claim 1, wherein the I is titanium oxide, the X is
the Y is
and the polyamic ester has the following chemical formula 2,

### Claim 4

A method of synthesizing an organic-inorganic hybrid polyamic ester, comprising:
synthesizing a polyamic acid by reacting a diamine monomer with a dianhydride; and
synthesizing a polyamic ester of the following chemical formula 1 by reacting the polyamic acid with an inorganic precursor,
wherein, in the chemical formula 1, the X is an alicyclic compound or an aromatic compound, the Y is at least one selected from a group consisting of an aliphatic compound, an alicyclic compound and an aromatic compound, and the I is at least one out of an inorganic element or a metal element,
wherein the dianhydride includes an aromatic or alicyclic compound.

### Claim 5 (depends on 4)

The method of claim 4, wherein the polyamic acid includes a number average molecular weight ranging from 500 to 100,000 g/mol.

### Claim 6 (depends on 4)

The method of claim 4, wherein the synthesizing of the polyamic acid comprises dissolving the diamine monomer and the dianhydride into a first solvent.

### Claim 7 (depends on 6)

The method of claim 6, wherein the first solvent is at least one selected from a group consisting of N,N-dimethyl acetamide, N,N-dimethyl formamide, and N-methylpyrrolidine.

### Claim 8 (depends on 4)

The method of claim 4, wherein the diamine monomer comprises at least one selected from a group consisting of an alphatic compound, an alicyclic compound and an aromatic compound.

### Claim 9 (depends on 8)

The method of claim 8, wherein the diamine monomer is at least one selected from a group consisting of 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4′-diamino octafluorobiphenyl, oxydianiline, m-phenylene diamine, 1,3-diaminopropane, and 1,2-bis(2-aminethoxy)ethane.

### Claim 10 (depends on 4)

The method of claim 4, wherein the dianhydride is at least one selected from a group consisting of 4,4′-oxydiphthalic anhydride, 4,4′-4,4′-hexafluoroisopropylidene, diphthalic anhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, pyromellitic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4,-cyclopentanetetracarboxylic dianhydride, and 1,2,4,5,-cyclohaxanetetracarboxylic dianhydride.

### Claim 11 (depends on 4)

The method of claim 4 wherein the synthesizing of the polyamic ester comprises introducing the inorganic precursor into a solution containing the polyamic acid with a catalyst.

### Claim 12 (depends on 11)

The method of claim 11, wherein the catalyst is at least one out of water, hydrochloric acid, nitric acid, sulfuric acid, and boric acid.

### Claim 13 (depends on 4)

The method of claim 4, wherein the synthesizing of the polyamic ester comprises dissolving the polyamic acid and the inorganic precursor into a second solvent with a catalyst.

### Claim 14 (depends on 13)

The method of claim 13, wherein the second solvent is at least one selected from a group consisting of N,N-dimethyl acetamide, N,N-dimethyl formamide, N-methylpyrrolidine, cyclohexanone and γ-butyrolactone.

### Claim 15 (depends on 4)

The method of claim 4, wherein the inorganic precursor comprises the following chemical formula 3,
A-O—I <Chemical formula 3>
wherein, in the chemical formula 3, the A is an alkyl group and the I comprises at least one element out of an inorganic element and a metal element or at least one alkoxide group or oxide group combined to the element.

### Claim 16

A method of fabricating a film, comprising:
dissolving a diamine monomer and a dianhydride into a first solvent and reacting the diamine monomer with the dianhydride to synthesize a polyamic acid;
introducing an inorganic precursor into a solution containing the polyamic acid or dissolving the polyamic acid and the inorganic precursor into a second solvent to react the polyamic acid with the inorganic precursor and to synthesize a polyamic ester of the following chemical formula 1; and
forming a film comprising the polyamic ester on a substrate,
wherein, in the chemical formula 1, the X is an alicyclic compound or an aromatic compound, the Y is at least one selected from a group consisting of an aliphatic compound, an alicyclic compound and an aromatic compound, and the I is at least one out of an inorganic element or a metal element.

### Claim 17 (depends on 16)

The method of claim 16, wherein the forming of the film comprising the polyamic ester, comprises:
coating a solution comprising the polyamic ester on the substrate; and
performing a dry process.

### Claim 18 (depends on 17)

The method of claim 17, wherein the dry process is performed at a temperature ranging from 150 to 200° C.

### Claim 19 (depends on 17)

The method of claim 17, further comprising heating the solution comprising the polyamic ester coated on the substrate and converting the polyamic ester to the related polyimide to fabricate a film where the I and the polyimide are mixed.

### Claim 20 (depends on 19)

The method of claim 19, wherein the conversion of the polyamic ester is performed at a temperature equal to or more than 200° C.
