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Organopolysiloxane compound and active energy ray curable composition containing the same

A curable composition and active energy ray technology, applied in organic chemistry, compounds of group 4/14 elements of the periodic table, chemical instruments and methods, etc., can solve problems such as corrosion of metal wiring parts and changes over time

Inactive Publication Date: 2019-06-21
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Generally, a positive type photoresist whose solubility to an alkaline developing solution is increased by exposing the resist pattern is often used, but the positive type photoresist has the following problems: Naphthoquinone diazide sulfonic acid used as a photosensitive agent produces sulfonic acid, which corrodes the metal wiring
[0010] However, in both of these patent documents 1 and 2, there is a problem that since the terminal of the obtained organopolysiloxane compound has a condensable functional group, it may change over time.

Method used

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  • Organopolysiloxane compound and active energy ray curable composition containing the same
  • Organopolysiloxane compound and active energy ray curable composition containing the same
  • Organopolysiloxane compound and active energy ray curable composition containing the same

Examples

Experimental program
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Effect test

Embodiment 1-1

[0112] 468.6g (2.0mol) of 3-acryloxypropyltrimethoxysilane, 262.3g (1.0mol) of 3-(trimethoxysilyl)propylsuccinic anhydride, 487.13g of hexamethyldisiloxane (3.0 mol) and 5.1 g of methanesulfonic acid were added to the reactor, and when it became uniform, 115.2 g of ion-exchanged water was added, and stirred at 25° C. for 4 hours. 25.3 g of Keyword 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was charged, stirred for 2 hours, and neutralized. Volatile components such as methanol were distilled off under reduced pressure, and pressure filtration was performed.

[0113] The obtained reactant was a liquid having a viscosity of 890 mPa·s at 25° C., a volatile component of 6.4% by mass, and a weight average molecular weight of 1180. The values ​​of a to g in the average formula (V) calculated from the results of NMR were a=0.29, b=0.13, c=0, d=0, e=0, f=0.58, and g=0.13, respectively.

Embodiment 1-2

[0115] 468.6g (2.0mol) of 3-acryloxypropyltrimethoxysilane, 524.7g (2.0mol) of 3-(trimethoxysilyl)propylsuccinic anhydride, 487.1g of hexamethyldisiloxane (3.0 mol) and 6.0 g of methanesulfonic acid were added to the reactor, and when it became uniform, 165.6 g of ion-exchanged water was added, and stirred at 25° C. for 2 hours. 30.1 g of Keyword 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added, stirred for 2 hours, and neutralized. Volatile components such as methanol were distilled off under reduced pressure, and pressure filtration was performed.

[0116] The obtained reactant was a liquid having a viscosity of 550 mPa·s at 25° C., a volatile content of 3.3% by mass, and a weight average molecular weight of 970. The values ​​of a to g in the average formula (V) calculated from the results of NMR were a=0.26, b=0.26, c=0, d=0, e=0, f=0.48, g=0.11, respectively.

Embodiment 1-3

[0118] 702.9g (3.0mol) of 3-acryloxypropyltrimethoxysilane, 262.3g (1.0mol) of 3-(trimethoxysilyl)propylsuccinic anhydride, 487.1g of hexamethyldisiloxane (3.0 mol) and 5.1 g of methanesulfonic acid were charged into the reactor, and when it became uniform, 147.6 g of ion-exchanged water was added, and stirred at 25° C. for 4 hours. 25.3 g of Keyword 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was charged, stirred for 2 hours, and neutralized. Volatile components such as methanol were distilled off under reduced pressure, and pressure filtration was performed.

[0119] The obtained reactant was a liquid having a viscosity of 190 mPa·s at 25° C., a volatile content of 4.1% by mass, and a weight average molecular weight of 1,210. The values ​​of a to g in the average formula (V) calculated from the results of NMR were a=0.42, b=0.14, c=0, d=0, e=0, f=0.44, g=0.08, respectively.

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Abstract

The present invention provides an organopolysiloxane compound and an active energy ray curable composition containing the same, particularly organopolysiloxane compound which is excellent in crack resistance, has a small change in hardness over time, and can be cured by an alkali development, and an active energy ray-curable composition which contains the organopolysiloxane compound and which canbe used as a negative resist material. The organopolysiloxane compound includes structural units shown as formulae (I) to (III), wherein the ratio of the total number of alkoxy and hydroxyl groups directly bonded to silicon atoms to the number of the silicon atoms is 0.3 or less; R1 and R4 represent a hydrogen atom, a methyl group, an ethyl group, a n-propyl group or an isopropyl group; R2 and R5represent a divalent hydrocarbon group having 1 to 10 carbon atoms; R3 represents a hydrogen atom or a methyl group; and R6 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a phenyl group, a (meth)acryloxypropyl group or a glycidoxypropyl group; n represents an integer satisfying 0 <= n <= 2; and m represents an integer satisfying 0 <= m <= 2.

Description

technical field [0001] The present invention relates to an organopolysiloxane compound and an active energy ray-curable composition containing the same, and more specifically, to an organopolysiloxane compound having an alkali-soluble site and an active energy ray-curable composition containing the same. Background technique [0002] With the increase in integration and speed of LSIs, it is necessary to reduce the size of resist patterns in the manufacturing process of semiconductor devices. [0003] Generally, a positive type photoresist whose solubility to an alkaline developing solution is increased by exposing the resist pattern is often used, but the positive type photoresist has the following problems: Naphthoquinonediazidesulfonic acid used as a photosensitive agent produces sulfonic acid, which corrodes metal wiring. [0004] On the other hand, such a problem does not occur in a negative photoresist that uses a mixture of a photocurable resin and an alkali-soluble r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/20C08G77/06G03F7/027G03F7/038
CPCC07F7/0838C08F2/48C08G77/14C08G77/20G03F7/0755
Inventor 藤本卓也吉川裕司
Owner SHIN ETSU CHEM IND CO LTD
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