IP Library Granted Patent US 7,517,917
Granted Patent B2
US 7,517,917 · App. 11/245,037 · Granted Apr 14, 2009

Composition for preparing nanoporous material comprising calixarene derivative

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Quick Facts
Patent No.
US 7,517,917
App. No.
11/245,037
Granted
Apr 14, 2009
Kind
B2
Abstract

A composition for preparing a nanoporous material. The composition comprises a thermostable matrix precursor, a calixarene derivative, and a solvent. The composition may enable formation of a low dielectric constant film in which nanopores with a size not larger than 50 Å are uniformly distributed.

Claims (28)

1. A composition for preparing a nanoporous material, comprising:

a thermostable matrix precursor having a glass transition temperature (Tg) of at least 400° C. which is selected from the group consisting of organic polysiloxane-based resin, organic silicates, partially condensed orthosilicates, polyimide-based polymers capable of undergoing imidization, polybenzocyclobutene-based polymers, and polyphenylene-based polymers;

a calixarene derivative represented by Formula 1 below:

wherein n is an integer of 3 to 10; R 1 is a C 1 -C 20 alkyl group; and R 2 is H, a C 2 -C 30 acyl group, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 carboxyl group, a C 1 -C 20 ester group, or a silicon compound represented by Sir 1 r 2 r 3 , in which r 1 , r 2 and r 3 are independently a C 1 -C 5 alkyl group, a C 1 -C 5 alkoxy group, or a C 6 -C 20 aryl group; and

a solvent which is capable of dissolving the above components.

2. The composition according to claim 1 , wherein the calixarene derivative is selected from the group consisting of 4-tert-1-methylcalix[4]arene, 4-tert-butyl -1 -acetylcalix[4]arene, 4-tert-1-methylbutylcalix[6]arene, and 4-tert-butyl-1 -acetylcax [6]arene.

3. The composition according to claim 1 , wherein the thermostable matrix precursor is a siloxane-based resin prepared by hydrolysis and condensation of a compound represented by Formula 6 below:

wherein R 1 is a hydrogen atom, a C 1 -C 3 alkyl group, or a C 6 -C 15 aryl group; X 1 , X 2 and X 3 are, independently, a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 10 alkoxy group, or a halogen atom, at least one of these substituents being a hydrolyzable functional group; m is an integer ranging from 1 to 10; and p is an integer ranging from 3 to 8; or

Formula 7 below:

wherein R 1 is a hydrogen atom, a C 1 -C 3 alkyl group, or a C 6 -C 15 aryl group; R 2 is a hydrogen atom, a C 1 -C 10 alkyl group, or SiX 1 X 2 X 3 , in which X 1 , X 2 and X 3 are, independently, a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 10 alkoxy group, or a halogen atom; and p is an integer between 3 and 8,

and a monomer represented by Formula 10 below:

RSiX 1 X 2 X 3   (10)

wherein R is a hydrogen atom, a C 1 -C 3 alkyl group, a C 3 -C 10 cycloalkyl group, or C 6 -C 15 aryl group; and X 1 , X 2 and X 3 are, independently, a C 1 -C 3 alkyl group, a C 1 -C 10 alkoxy group or a halogen atom, using an acid catalyst and water in the presence of an organic solvent.

4. The composition according to claim 1 , wherein the percentage content of the calixarene derivative in the composition is in the range of 0.1%-95% by weight, based on the sum of the amounts of the matrix precursor and calixarene derivative.

5. The composition according to claim 1 , wherein the percentage content of the solvent in the composition is in the range of 20%-99.9% by weight.

6. The composition according to claim 1 , wherein the solvent is selected from the group consisting of aromatic hydrocarbons, ketones, ethers, acetates, amides, γ-butyrolactones, alcohols, silicon solvents, and mixtures thereof.

7. The composition according to claim 5 , wherein the solvent is selected from the group consisting of anisole, xylene, mesitylene, methyl isobutyl ketone, 1-methyl-2-pyrrolidinone, acetone, tetrahydrofuran, isopropyl ether, ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, dimethylacetamide, dimethylformamide, γ-butyrolactone, isopropyl alcohol, butyl alcohol, octyl alcohol, silicon solvents, and mixtures thereof.

8. A method for forming a low dielectric constant film, comprising the steps of: coating the composition according to claim 1 on a semiconductor substrate by spin coating, dip coating, spray coating, flow coating, or screen printing; evaporating the solvent from the coated substrate; and heat-curing the coated substrate to 150-600° C. under an inert atmosphere or vacuum.

9. A nanoporous structure produced using the composition according to claim 1 .

10. A method of making an article comprising incorporating the nanoporous structure according to claim 9 into said article.

11. The method according to claim 10 , wherein said article is a heat resistant material.

12. The method according to claim 10 , wherein said article is an electrical insulator.

13. The method according to claim 10 , wherein said article is an absorbent.

14. The method according to claim 10 , wherein said article is a catalyst support.

15. A heat resistant material comprising the nanoporous structure according to claim 9 .

16. An electrical insulator comprising the nanoporous structure according to claim 9 .

17. An adsorbent comprising the nanoporous structure according to claim 9 .

18. A support for a catalyst comprising the nanoporous structure according to claim 9 .

Assignments (4)
CHANGE OF NAME Recorded Aug 6, 2010
From: SAMSUNG CORNING PRECISION GLASS CO., LTD.
To: SAMSUNG CORNING PRECISION MATERIALS CO., LTD.
Reel/Frame 024804/0238 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE/ASSIGNOR PREVIOUSLY RECORDED ON REEL 020624 FRAME 0240. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER. Recorded May 16, 2008
From: SAMSUNG CORNING CO., LTD.
To: SAMSUNG CORNING PRECISION GLASS CO., LTD.
Reel/Frame 020956/0832 →
MERGER Recorded Mar 10, 2008
From: SAMSUNG CORNING PRECISION GLASS CO., LTD.
To: SAMSUNG CORNING CO., LTD.
Reel/Frame 020624/0240 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2006
From: YIM, JIN HEONG; LEE, KWANG HEE
To: SAMSUNG CORNING CO., LTD.
Reel/Frame 017473/0517 →