IP Library Granted Patent US 9,091,920
Granted Patent B2
US 9,091,920 · App. 14/117,449 · Granted Jul 28, 2015

Photosensitive siloxane resin composition

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Quick Facts
Patent No.
US 9,091,920
App. No.
14/117,449
Granted
Jul 28, 2015
Kind
B2
Abstract

[Object] To provide a photosensitive siloxane resin composition excellent in alkali-solubility and in sensitivity, and also to provide a pattern-formation method employing that. [Means] The present invention provides a photosensitive siloxane resin composition comprising: a siloxane resin having silanol groups or alkoxysilyl groups, a crown ether, a photosensitive material, and an organic solvent. This photosensitive composition is cast on a substrate, subjected to imagewise exposure, treated with an alkali aqueous solution, and cured to form a pattern.

Claims (23)

1. A positive working photosensitive siloxane resin composition comprising

a siloxane resin having silanol groups or alkoxysilyl groups, wherein said siloxane resin comprises at least one structure selected from the group consisting of a silicone skeleton, a silsesquioxane skeleton and a silica skeleton, wherein the silicone skeleton comprises 10 mole % or less of the total siloxane resin,

a crown ether, selected from the group consisting of 21-crown-7-ether, 18-crown-6-ether, 15-crown-5-ether, 12-crown-4-ether, dibenzo-21-crown-7-ether, dibenzo-18-crown-6-ether, dibenzo-15-crown-5-ether, dibenzo-12-crown-4-ether, dicyclohexyl-21-crown-7-ether, dicyclohexyl-18-crown-6-ether, dicyclo-hexyl-15-crown-5-ether, and dicyclohexyl-12-crown-4-ether.

a photosensitive additive chosen from a diazonaphthoquinone derivative where a phenolic hydroxyl-containing compound is combined via an ester bond with a naphthoquinonediazidesulfonic acid and,

an organic solvent.

2. The photosensitive siloxane resin composition according to claim 1 , wherein said siloxane resin has a silsesquioxane structure.

3. The photosensitive siloxane resin composition according to claim 1 , wherein said siloxane resin has a weight average molecular weight of 400 to 5000.

4. A pattern formation method comprising the steps of:

coating a substrate with the photosensitive siloxane resin composition according to claim 1 , to form a coating;

subjecting said coating to imagewise exposure;

treating the exposed coating with an alkali aqueous solution; and then

curing the treated coating at 150 to 450° C. in air or in an inert gas atmosphere.

5. A siliceous film produced according to the method of claim 4 .

6. The photosensitive siloxane resin composition according to claim 1 , where the crown ether is selected from the group consisting of 18-crown-6-ether, and 15-crown-5-ether.

7. The photosensitive siloxane resin composition according to claim 1 , where the siloxane resin having silanol groups or alkoxysilyl groups, is obtained by hydrolysis of one or more alkoxysilane compounds represented by formula (A);

(R 1 ) a Si(OR 2 ) 4-a   (A)

where R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aralkyl group having 15 or less carbon atoms and having no hydrogen atom connecting to the α-position carbon atom, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted alkenyl group having 1 to 6 carbon atoms, R 2 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and a is an integer of 0 to 3.

8. The photosensitive siloxane resin composition according to claim 1 , where the siloxane resin having silanol groups or alkoxysilyl groups, is obtained by hydrolysis of one or more halosilane compounds represented by the following formula (B);

(R 1 ) a SiX 4-a   (B),

where R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aralkyl group having 15 or less carbon atoms and having no hydrogen atom connecting to the α-position carbon atom, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted alkenyl group having 1 to 6 carbon atoms, X, is a halogen atom, and a is an integer of 0 to 3.

9. The photosensitive siloxane resin composition according to claim 1 , where the siloxane resin having silanol groups or alkoxysilyl groups, is obtained by hydrolysis of a combination of compound (A) and (B).

10. The photosensitive siloxane resin composition according to claim 1 , where the naphthoquinonediazidesulfonic acid is 4-napthoquinonediazidesulfonic acid or 5-napthoquinonediazidesulfonic acid.

11. The photosensitive siloxane resin composition according to claim 1 , where the phenolic hydroxyl compounds is selected from the group consisting of the following compounds;

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2015
From: AZ ELECTRONIC MATERIALS USA CORP.
To: MERCK PATENT GMBH
Reel/Frame 034742/0689 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2014
From: SEKITO, TAKASHI; YOKOYAMA, DAISHI; FUKE, TAKASHI; TASHIRO, YUJI; NONAKA, TOSHIAKI; TANAKA, YASUAKI
To: AZ ELECTRONIC MATERIALS USA CORP.
Reel/Frame 034569/0685 →