IP Library Granted Patent US 10,606,173
Granted Patent B2
US 10,606,173 · App. 16/087,713 · Granted Mar 31, 2020

Photosensitive siloxane composition

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Quick Facts
Patent No.
US 10,606,173
App. No.
16/087,713
Granted
Mar 31, 2020
Kind
B2
Abstract

[Object] To provide a composition capable of forming a cured film having low permittivity and excellence in chemical resistance, in heat resistance and in resolution; and further to provide a production process employing the composition. [Means] The present invention provides a composition comprising: an alkali-soluble resin, namely, a polymer comprising a carboxyl-containing polymerization unit and an alkoxysilyl-containing polymerization unit; a polysiloxane; a diazonaphthoquinone derivative; a compound generating acid or base when exposed to heat or light; and a solvent.

Claims (63)

1. A composition comprising:

an alkali-soluble resin which is a polymer comprising a carboxyl-containing polymerization unit and an alkoxysilyl-containing polymerization unit,

a polysiloxane,

a diazonaphthoquinone derivative,

a compound generating acid or base when exposed to heat or light, and

a solvent and

wherein said compound generating acid or base when exposed to heat or light is a photo acid- or base-generator whose absorbance ratio at 365 nm/436 nm or at 365 nm/405 nm is 5/1 or more.

2. The composition according to claim 1 , wherein said carboxyl-containing polymerization unit is derived from an unsaturated carboxylic acid, an unsaturated carboxylic anhydride, or a mixture thereof.

3. The composition according to claim 1 , wherein said alkoxysilyl-containing polymerization unit is derived from a monomer represented by the following formula (I):

X—(CH 2 ) a —Si(OR) b (CH 3 ) 3-b   (I)

in which

X is a vinyl, styryl or (meth)acryloyloxy group;

R is methyl or ethyl group;

a is an integer of 0 to 3; and

b is an integer of 1 to 3.

4. The composition according to claim 1 , wherein said polysiloxane is derived from a monomer represented by the following formula (II):

R 1 [Si(OR 2 ) 3 ] p   (II)

in which

p is an integer of 1 to 3;

R 1 is hydrogen or a p-valent straight, branched or cyclic hydrocarbon group which has 20 or less carbon atoms and which may contain oxygen or nitrogen, provided that any hydrogen of the hydrocarbon group may be replaced with fluorine; and

each R 2 is independently hydrogen or an alkyl group having 1 to 10 carbon atoms.

5. The composition according to claim 1 , wherein said compound generating acid or base when exposed to heat or light is a photo acid- or base-generator whose absorbance ratio at 365 nm/436 nm or at 365 nm/405 nm is 10/1 or more.

6. The composition according to claim 1 , wherein said alkali-soluble resin has a weight average molecular weight of 3000 to 50000.

7. The composition according to claim 1 , wherein said polysiloxane has a weight average molecular weight of 800 to 15000.

8. The composition according to claim 1 , wherein the mixing ratio of said alkali-soluble resin and said polysiloxane is 5:95 to 95:5 by weight.

9. A method for forming a cured film, comprising:

coating a substrate with the composition according to claim 1 , to form a coating film;

exposing the coating film to light;

developing the exposed film with an alkali developer, to form a pattern; and

heating the obtained pattern.

10. The method for forming a cured film, according to claim 9 ; which further comprises the step of exposing the whole film surface to light before the step of heating the obtained pattern.

11. A cured film produced by a method comprising:

coating a substrate with the composition according to claim 1 , to form a coating film;

exposing the coating film to light;

developing the exposed film with an alkali developer, to form a pattern; and

heating the obtained pattern.

12. A device comprising the cured film according to claim 11 .

13. The composition according to claim 2 , wherein said alkoxysilyl-containing polymerization unit is derived from a monomer represented by the following formula (I):

X—(CH 2 ) a —Si(OR) b (CH 3 ) 3-b   (I)

in which

X is a vinyl, styryl or (meth)acryloyloxy group;

R is methyl or ethyl group;

a is an integer of 0 to 3;

b is an integer of 1 to 3.

14. The composition according to claim 2 , wherein said alkoxysilyl-containing polymerization unit is derived from a monomer represented by the following formula (I):

X—(CH 2 ) a —Si(OR) b (CH 3 ) 3-b   (I)

in which

X is a vinyl, styryl or (meth)acryloyloxy group;

R is methyl or ethyl group;

a is an integer of 0 to 3;

b is an integer of 1 to 3 and

said polysiloxane is derived from a monomer represented by the following formula (II):

R 1 [Si(OR 2 ) 3 ] p   (II)

in which

p is an integer of 1 to 3;

R 1 is hydrogen or a p-valent straight, branched or cyclic hydrocarbon group which has 20 or less carbon atoms and which may contain oxygen or nitrogen, provided that any hydrogen of the hydrocarbon group may be replaced with fluorine; and

each R 2 is independently hydrogen or an alkyl group having 1 to 10 carbon atoms.

15. The composition according to claim 14 , wherein said compound generating acid or base when exposed to light is a photo acid- or base-generator whose absorbance ratio at 365 nm/436 nm or at 365 nm/405 nm is 10/1 or more.

16. The composition according to claim 14 , wherein said compound generating acid or base when exposed to light is a photo acid-generator whose absorbance ratio at 365 nm/436 nm or at 365 nm/405 nm is 5/1 or more.

17. The composition according to claim 14 , wherein said compound generating acid or base when exposed to light is a photo base-generator whose absorbance ratio at 365 nm/436 nm or at 365 nm/405 nm is 5/1 or more.

18. The composition according to claim 14 , wherein said alkali-soluble resin has a weight average molecular weight of 3000 to 50000, said polysiloxane has a weight average molecular weight of 800 to 15000 and the mixing ratio of said alkali-soluble resin and said polysiloxane is 5:95 to 95:5 by weight.

19. The composition according to claim 1 , wherein said compound generating acid or base when exposed to heat or light is a photo acid- or base-generator whose absorbance ratio at 365 nm/436 nm or at 365 nm/405 nm is 100/1 or more.

20. The composition according to claim 19 , wherein said compound generating acid or base is exposed to light.

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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2018
From: TAKAHASHI, MEGUMI; YOKOYAMA, DAISHI; YOSHIDA, NAOFUMI; TANIGUCHI, KATSUTO; KUZAWA, MASAHIRO
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.A.R.L.
Reel/Frame 046948/0255 →