IP Library Granted Patent US 10,513,632
Granted Patent B2
US 10,513,632 · App. 14/913,821 · Granted Dec 24, 2019

Film-forming composition and film-forming method using same

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Quick Facts
Patent No.
US 10,513,632
App. No.
14/913,821
Granted
Dec 24, 2019
Kind
B2
Abstract

[Problem] To provide a film forming composition and a method for preparing a film with which it is possible to form a film having excellent gas barrier performance. [Means for Solution] Disclosed is a film forming composition comprising: a polysiloxane that does not include a hydroxyl group or a carboxyl group; a polysilazane; and an organic solvent. Also disclosed is a method for preparing a film comprising: coating a substrate with said composition; and exposing the same to light.

Claims (43)

1. A film forming composition consisting essentially of:

a polysiloxane represented by the following general formula (1):

a polysilazane and

an organic solvent,

wherein,

R 11 is a group each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an amino group, and an alkylsilyl group, and may be substituted by one or more of groups selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an amino group, a silyl group and an alkylsilyl group when R 11 is a group other than a hydrogen atom;

the total number of amino groups and alkoxy groups contained in all of R 11 in the formula is not more than 5% of the total number of R 11 ; and

R 12 is each independently a hydrocarbon group having 1 to 8 carbon atoms or —R 13 —N—R 14 2 , wherein R 13 is a hydrocarbon group having 1 to 5 carbon atoms, and R 14 is each independently hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, wherein n1 is the number of repeat units which cannot be 0.

2. The film forming composition according to claim 1 , wherein R 11 is an alkyl group having 1 to 3 carbon atoms.

3. The film forming composition according to claim 1 , wherein R 12 is a group selected from the group consisting of a methyl group, an ethyl group, a propyl group, an aminomethyl group, aminoethyl group, aminopropyl group, and N-ethylamino-2-methylpropyl group.

4. The film forming composition according to claim 1 , wherein the polysilazane has a structural unit represented by the following general formula (2):

wherein,

R 21 is a group each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an amino group, and a silyl group; at least one of R 21 in the formula is a hydrogen atom; and the group other than hydrogen atom may be substituted by one or more of groups selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an amino group, a silyl group, and an alkylsilyl group, wherein n2 is the number of repeat units which cannot be 0.

5. The film forming composition according to claim 4 , wherein R 21 is a group each independently selected from the group consisting of hydrogen, an alkyl group, an alkenyl group, an aryl group, an alkylsilyl group, and an alkoxysilyl group.

6. The film forming composition according to claim 1 , wherein the compounding amount of polysiloxane is 0.01 to 25 parts by weight based on 100 parts by weight of the polysilazane.

7. The film forming composition according to claim 1 , wherein the organic solvent comprises one or more of an aromatic hydrocarbon, a saturated hydrocarbon compound, an alicyclic hydrocarbon compound or an alkyl ether.

8. A method for preparing a film comprising the following steps:

(1) a coating step to coat the film forming composition according to claim 1 on a substrate to form a coating film thereon, and

(2) an exposure step to expose the coating film to light.

9. A method for preparing a film according to claim 8 , wherein the substrate is a plastic film.

10. A method for preparing a film according to claim 8 , wherein thickness of the coating film is not less than 10 nm and not more than 900 nm.

11. A method for preparing a film according to claim 8 , wherein wavelength of the light is 161 to 248 nm.

12. A method for preparing a film according to claim 8 , wherein the exposure step is carried out in an inert gas atmosphere.

13. A method for preparing a film according to claim 8 , wherein the coating film is not subjected to the temperature of 200° C. or higher while a film is formed by curing the coating film.

14. A film produced by the method according to claim 8 .

15. The film forming composition according to claim 2 , wherein R 12 is a group selected from the group consisting of a methyl group, an ethyl group, a propyl group, an aminomethyl group, aminoethyl group, aminopropyl group, and N-ethylamino-2-methylpropyl group.

16. The film forming composition according to claim 2 , wherein the polysilazane has a structural unit represented by the following general formula (2):

wherein,

R 21 is a group each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an amino group, and a silyl group; at least one of R 21 in the formula is a hydrogen atom; and the group other than hydrogen atom may be substituted by one or more of groups selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an amino group, a silyl group, and an alkylsilyl group, wherein n2 is the number of repeat units which cannot be 0.

17. The film forming composition according to claim 16 , wherein R 21 is a group each independently selected from the group consisting of hydrogen, an alkyl group, an alkenyl group, an aryl group, an alkylsilyl group, and an alkoxysilyl group.

18. The film forming composition according to claim 1 , wherein the film forming composition further comprises an amino compound or a metal complex compound.

19. The film forming composition according to claim 1 , wherein the polysiloxane represented by the general formula (1) is selected from the group consisting of

wherein n1 and n3 denote the number of repeat units which cannot be 0,

and further where the polysilazane has a structural unit selected from the group consisting of

 wherein n2 is the number of repeat units which cannot be 0.

20. A film forming composition consisting of:

a polysiloxane represented by the following general formula (1):

a polysilazane having a molecular weight of 1,000 to 50,000 and

an organic solvent,

wherein,

R 11 is a group each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an amino group, and an alkylsilyl group, and may be substituted by one or more of groups selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an amino group, a silyl group and an alkylsilyl group when R 11 is a group other than a hydrogen atom;

the total number of amino groups and alkoxy groups contained in all of R 11 in the formula is not more than 5% of the total number of R 11 ; and

R 12 is each independently a hydrocarbon group having 1 to 8 carbon atoms or —R 13 —N—R 14 2 , wherein R 13 is a hydrocarbon group having 1 to 5 carbon atoms, and R 14 is each independently hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, wherein n1 is the number of repeat units which cannot be 0.

Assignments (5)
MERGER Recorded Jul 27, 2020
From: RIDGEFIELD ACQUISITION
To: AZ ELECTRONIC MATERIALS S.À R.L.
Reel/Frame 053323/0591 →
CHANGE OF LEGAL ENTITY Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS S.À R.L.
To: AZ ELECTRONIC MATERIALS GMBH
Reel/Frame 053323/0760 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS GMBH
To: MERCK PATENT GMBH
Reel/Frame 053323/0770 →
MERGER Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
To: RIDGEFIELD ACQUISITION
Reel/Frame 053324/0198 →
CHANGE OF ADDRESS Recorded Jan 12, 2017
From: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
Reel/Frame 041345/0585 →