IP Library Granted Patent US 9,817,312
Granted Patent B2
US 9,817,312 · App. 15/031,668 · Granted Nov 14, 2017

Silicon-containing heat- or photo-curable composition

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Quick Facts
Patent No.
US 9,817,312
App. No.
15/031,668
Granted
Nov 14, 2017
Kind
B2
Abstract

A heat- or photo-curable composition comprising: a polysiloxane which is produced by reacting a silicon compound (i) represented by the formula: R 1 n Si(X) 4-n (wherein R 1 represents an alkyl group, an aryl group or the like; X represents a chlorine atom or an alkoxy group; and n represents 0 to 2) with a silicon compound (ii) represented by the formula (b) or (c) (wherein R 2 to R 7 independently represent an alkyl group or the like; M 1 and M 2 independently represent an arylene group, an alkylene group or the like; and Y 1 to Y 6 independently represent a chlorine atom or an alkoxy group) in the presence of an alkali catalyst or an acid catalyst; a polymerization initiator which enables the generation of an acid or a base by the action of heat or light; and a solvent. The composition enables the formation of a thick film. When the composition is coated onto a substrate, is then heated or exposed to light, is then developed if necessary, and is then heated and cured at a low temperature, a cured film can be formed.

Claims (33)

1. A heat- or photo-curable composition comprising;

(I) polysiloxane obtained by reacting at least one of silicon compounds (i) represented by the formula (a):

R 1 n Si(X) 4-n   (a)

wherein, R 1 represents a hydrogen atom, a liner or branched alkyl group having 1 to 20 carbon atoms in which any —CH 2 — group may be replaced by a —O—, —C═C— or —CO— group and any hydrogen atom may be replaced by a fluorine atom, and which may have a substituent, an aryl group having 6 to 20 carbon atoms in which any hydrogen atom may be replaced by a fluorine atom and which may have a substituent, a cycloalkyl group having 3 to 20 carbon atoms in which any hydrogen atom may be replaced by a fluorine atom and which may have a substituent, or an alkenyl group having 2 to 20 carbon atoms in which any hydrogen atom may be replaced by a fluorine atom and which may have a substituent, X represents a chlorine atom or an ethoxy group, and n is 0 to 2, and

at least one of silicon compounds (ii) represented by the formula (b):

wherein, R 2 to R 5 may be the same or different from each other and represent an alkyl group which may be substituted, an aryl group which may be substituted, or an alkenyl group which may be substituted, M 1 represents an arylene group which may be substituted, or a biphenylene group which may be substituted, or an alkynylene group having 2 to 4 carbon atoms which may be substituted, Y 1 and Y 2 may be the same or different from each other and represent a chlorine atom or an ethoxy group, or

represented by the formula (c):

wherein, R 6 and R 7 may be the same or different from each other and represent an alkyl group which may be substituted, an aryl group which may be substituted, or an alkenyl group which may be substituted, M 2 represents an arylene group which may be substituted, or a biphenylene group which may be substituted, and Y 3 to Y 6 may be the same or different from each other and represent a chlorine atom or an ethoxy group,

under an alkali catalyst or an acid catalyst,

(II) a polymerization initiator which enables the generation of an acid or a base by the action of heat or light, and

(III) a solvent.

2. The heat- or photo-curable composition according to claim 1 , wherein a dissolution rate of a film after prebaking of the polysiloxane (I) in a 2.38 weight % tetramethylammonium hydroxide aqueous solution is 50 to 20,000 Å/second.

3. The heat- or photo-curable composition according to claim 2 , wherein a ratio of the silicon compounds (ii) to the whole silicon compounds is 0.1 to 40 mol %.

4. The heat- or photo-curable composition according to claim 2 , wherein the polymerization initiator (II) is contained by 0.001 to 10 weight parts to polysiloxane (I) by 100 weight parts.

5. The heat- or photo-curable composition according to claim 1 , wherein a ratio of the silicon compounds (ii) to the whole silicon compounds is 0.1 to 40 mol %.

6. The heat- or photo-curable composition according to claim 5 , wherein the polymerization initiator (II) is contained by 0.001 to 10 weight parts to polysiloxane (I) by 100 weight parts.

7. The heat- or photo-curable composition according to claim 1 , wherein the polymerization initiator (II) is contained by 0.001 to 10 weight parts to polysiloxane (I) by 100 weight parts.

8. The heat- or photo-curable composition according to claim 1 , wherein at least one kind of additives selected from a group consisting of a developer dissolution accelerator, a scum remover, an adhesion enhancer, a polymerization inhibitor, a defoaming agent, a surfactant, and a photosensitizer is further contained.

9. A method for preparing a cured film which comprises the steps of: coating the heat- or photo-curable composition according to any one of claims 1 to 5 to a substrate to form a coating film; heating or light-exposing the coating film to generate an acid or a base; and curing the heated or light-exposed coating film by thermal process.

10. The method for preparing a cured film according to claim 9 , wherein a photo-curable composition is used as the heat- or photo-curable composition and a step of developing a light-exposed coating film is further provided after the light-exposing step of the photo-curable composition wherein in the light exposing step, g-line, h-line, or l line is irradiating the light-exposed coating film.

11. A cured film which is formed from the heat- or photo-curable composition according to claim 1 .

12. An element which comprises the cured film according to claim 11 .

13. The heat- or photo-curable composition according to claim 1 , wherein the silicon compounds (i) represented by the formula (a) is selected from the group consisting of compounds having formula (d), (e), and (f)

R 1 2 Si(X) 2   (d)

R 1 Si(X) 3   (e)

Si(X) 4   (f).

14. The heat- or photo-curable composition according to claim 13 , wherein the silicon compounds (i) represented by the formula (a) is the compounds having formula (d).

15. The heat- or photo-curable composition according to claim 13 , wherein the silicon compounds (i) represented by the formula (a) is the compounds having formula (e).

16. The heat- or photo-curable composition according to claim 13 , wherein the silicon compounds (i) represented by the formula (a) is the compounds having formula (f).

17. The heat or photo curable composition according to claim 1 , wherein the silicon compounds (ii) represented by the formula (b) is selected from the group consisting of 1,4-bis(dimethylethoxysilyl)benzene, and 1,4-bis(diethylchlorosilyl)benzene.

18. The heat or photo curable composition according to claim 1 , wherein the silicon compounds (ii) represented by the formula (c) is 1,4-bis(methyldiethoxysilyl)benzene.

19. The heat or photo curable composition according to claim 1 , wherein the silicon compounds (ii) represented by the formula (b) is 1,4-bis(dimethylethoxysilyl)benzene.

20. The heat or photo curable composition according to claim 1 , wherein the silicon compounds (ii) are represented by the formula (b).

Assignments (6)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2016
From: YOSHIDA, NAOFUMI; TASHIRO, YUJI
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.A.R.L.
Reel/Frame 038830/0770 →