IP Library Granted Patent US 8,993,214
Granted Patent B2
US 8,993,214 · App. 14/117,433 · Granted Mar 31, 2015

Positive photosensitive siloxane composition

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Quick Facts
Patent No.
US 8,993,214
App. No.
14/117,433
Granted
Mar 31, 2015
Kind
B2
Abstract

A positive photosensitive siloxane composition comprising at least three types of following polysiloxanes (A), (B) and (C) obtained by hydrolyzing and condensing a silane compound represented by general formula (1) R 1 n Si (OR 2 ) 4-n , a diazonaphthoquinone derivative, and a solvent: a polysiloxane (A) such that if pre-baked the film thereof will be soluble in a 5 weight % TMAH aqueous solution and the solution rate of said film will be 1,000 Å/sec or less; a polysiloxane (B) such that if pre-baked the solution rate of the film thereof will be 4,000 Å/sec or more relative to a 2.38 weight % TMAH aqueous solution; and a polysiloxane (C) such that if pre-baked the solution rate of the film thereof will be between 200 and 3,000 Å/sec relative to a 2.38 weight % TMAH aqueous solution. (In the formula, R 1 represents a C1-20 linear or branched cyclic alkyl group, in which any methylene may be substituted by oxygen, or a C6-20 aryl group, in which any hydrogen may be substituted by fluorine; n represents a 0 or a 1; and R 2 represents a C1-5 alkyl group.)

Claims (27)

1. A positive photosensitive siloxane composition comprising polysiloxane (I), a diazonaphthoquinone derivative (II), and a solvent (III),

wherein the polysiloxane (I) contains at least one of polysiloxane (Ia) below, at least one of polysiloxane (Ib) below, and at least one of polysiloxane (Ic) below,

(A) Polysiloxane (Ia): a polysiloxane, where a prebaked film of which is soluble in a 5 wt % tetramethylammonium hydroxide aqueous solution and which has a dissolution rate of 1,000 Å/second or less in a 5 wt % tetramethylammonium hydroxide aqueous solution and is obtained by hydrolyzing and condensing, in the presence of an acidic or basic catalyst, a silane compound represented by the formula (1);

R 1 n Si(OR 2 ) 4-n   (1)

wherein R 1 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, in which any methylene group may be replaced by an oxygen atom, or an aryl group having 6 to 20 carbon atoms, in which any hydrogen atom may be replaced by a fluorine atom, R 2 represents an alkyl group having 1 to 5 carbon atoms, and n is 0 or 1,

(B) Polysiloxane (Ib): a polysiloxane, where a prebaked film of which has a dissolution rate of 4,000 Å/second or more in a 2.38 wt % tetramethylammonium hydroxide aqueous solution and which is obtained by hydrolyzing and condensing the silane compound represented by the formula (1) in the presence of an acidic or basic catalyst,

(C) Polysiloxane (Ic): a polysiloxane, where a prebaked film of which has a dissolution rate of 200 Å/second or more and 3,000 Å/second or less in a 2.38% tetramethylammonium hydroxide aqueous solution and which is obtained by hydrolyzing and condensing the silane compound represented by the formula (1) in the presence of an acidic or basic catalyst.

2. The positive photosensitive siloxane composition according to claim 1 , wherein the polysiloxane (Ia) is obtained by hydrolyzing and condensing the aforementioned silane compound in the presence of a basic catalyst.

3. The positive photosensitive siloxane composition according to claim 1 , wherein the ratio of a total weight of polysiloxanes (Ia) and (Ib) to a weight of polysiloxane (Ic) is 95/5 to 50/50.

4. The positive photosensitive siloxane composition according to claim 1 , wherein the weight ratio of polysiloxanes (Ia) to polysiloxane (Ib) is 30/70 to 70/30.

5. The positive photosensitive siloxane composition according to claim 1 , wherein silane compounds which constitute the polysiloxane (I) contains from 5 mole-% to 30 mole-% of silane compounds, ‘n’ in the formula (1) of which is zero.

6. The positive photosensitive siloxane composition according to claim 1 , wherein silane compounds which constitute at least one of each of polysiloxanes (Ia), (Ib), and (Ic) contain from 20 mole-% to 80 mole-% of silane compounds on an average, and in which R 1 in the formula (1) is a methyl group.

7. The positive photosensitive siloxane composition according to claim 6 , wherein silane compounds which constitute the polysiloxane (I) contain 20 mole-% to 80 mole-% of a silane compound on an average, and in which R 1 in the formula (1) is a methyl group.

8. A cured film which is formed from the positive photosensitive siloxane composition according to claim 1 .

9. An element having the cured film according to claim 8 .

10. The positive photosensitive siloxane composition according to claim 1 wherein R 1 of the formula (1) is selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a t-butyl group, a n-hexyl group, a n-decyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, and a cyclohexyl group.

11. The positive photosensitive siloxane composition according to claim 1 wherein the aryl group having 6 to 20 carbon atoms in which any hydrogen atom may be replaced by a fluorine group is selected from the group consisting of a phenyl group, a tolyl group, and a naphthyl group.

12. The positive photosensitive siloxane composition according to claim 1 wherein R 2 of the formula (1) is selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, and a n-butyl group.

13. The positive photosensitive siloxane composition according to claim 1 wherein the silane represented by formula (1) in which n is 1 is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, methyltriisopropoxysilane, methyltri-n-butoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltriisopropoxysilane, ethyltri-n-butoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, n-butyltrimethoxysilane, n-butyltriethoxysilane, n-hexyltrimethoxysilane, n-hexyltriethoxysilane, decyltrimethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, naphthyltrimethoxysilane, naphthyltriethoxysilane, naphthyltriisopropoxysilane, naphthytri-n-butoxysilane, trifluoromethyltrimethoxysilane, trifluoromethyltriethoxysilane, and 3,3,3-trifluoropropyltrimethoxysilane.

14. The positive photosensitive siloxane composition according to claim 1 wherein the silane represented by formula (1) in which n is 1 is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane.

15. The positive photosensitive siloxane composition according to claim 1 wherein the silane represented by formula (1) in which n is 0 is selected from the group consisting of tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, and tetrabutoxysilane.

16. The positive photosensitive siloxane composition according to claim 1 wherein the silane represented by formula (1) in which n is 0 is selected from the group consisting of tetramethoxysilane and tetraethoxysilane.

17. The positive photosensitive siloxane composition according to claim 1

where the diazonaphthoquinone derivative (II) is a compound in which a naphthoquinonediazide sulfonic acid is ester-linked to a compound having a phenolic hydroxyl group.

18. The positive photosensitive siloxane composition according to claim 17 where the compound with a phenolic hydroxyl group has one or more of phenolic hydroxyl groups.

19. The positive photosensitive siloxane composition according to claim 17 where the naphthoquinonediazide sulfonic is 4-naphthoquinonediazidesulfonic acid or 5-naphthoquinonediazidesulfonic acid.

20. The positive photosensitive siloxane composition according to claim 17 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 12, 2014
From: YOKOYAMA, DAISHI; FUKE, TAKASHI; TASHIRO, YUJI; SEKITO, TAKASHI; NONAKA, TOSHIAKI
To: AZ ELECTRONIC MATERIALS USA CORP.
Reel/Frame 034485/0445 →