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

A curable composition and technology of active energy rays, applied in the field of organopolysiloxane compounds and active energy ray curable compositions containing them, and active energy ray curable compositions, can solve the corrosion of metal wiring parts, etc. question

Active Publication Date: 2022-07-05
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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
[0012] However, an organopolysiloxane compound that satisfies both hardness and toughness of a cured product and imparts active energy ray curability to an alkali-developable cured film is not yet known.

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
Comparison scheme
Effect test

Embodiment 1-1

[0117] 3-Isocyanatopropyltrimethoxysilane (KBM-9007, manufactured by Shin-Etsu Chemical Co., Ltd.) was added while stirring 348.3 g (3.0 mol) of hydroxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.) in the reactor. After production) 615.9 g (3.0 mol), the mixture was stirred at 25° C. for 1 hour to obtain 964.2 g (3.0 mol) of a compound represented by the following formula (VI).

[0118] Thereto were added 262.3 g (1.0 mol) of 3-(trimethoxysilyl)propyl succinic anhydride, 487.1 g (3.0 mol) of hexamethyldisiloxane, and 7.2 g of methanesulfonic acid, and added when it became uniform. 147.6 g of ion-exchanged water was stirred at 25°C for 4 hours. 35.9 g of Kaiwa Chemical Industry Co., Ltd. 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was put in, stirred for 2 hours, and neutralized. Volatile components such as methanol were distilled off under reduced pressure, followed by pressure filtration.

[0119] The obtained reactant was a viscou...

Embodiment 1-2

[0123] 642.8 g (2.0 mol) of the compound represented by the above formula (VI), 524.7 g (2.0 mol) of 3-(trimethoxysilyl)propylsuccinic anhydride, 487.1 g (3.0 mol) of hexamethyldisiloxane , 6.9 g of methanesulfonic acid was put into the reactor, 165.6 g of ion-exchanged water was added when it became uniform, and the mixture was stirred at 25° C. for 2 hours. 34.5 g of Kaiwa Chemical Industry Co., Ltd. 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was put in, stirred for 2 hours, and neutralized. Volatile components such as methanol were distilled off under reduced pressure, followed by pressure filtration.

[0124] The obtained reactant was a viscous liquid at 25°C having a viscosity of 3200 mPa·s at 25°C, a volatile content of 2.5% by mass, and a weight average molecular weight of 1530. The values ​​of a to g in the average formula (IV) calculated from the results of NMR were a=0.22, b=0.23, c=0, d=0, e=0, f=0.55, and g=0.02, respectively.

Embodiment 1-3

[0126] 642.8 g (2.0 mol) of the compound represented by the above formula (VI), 262.3 g (1.0 mol) of 3-(trimethoxysilyl)propylsuccinic anhydride, 136.2 g (1.0 mol) of methyltrimethoxysilane, 487.1 g (3.0 mol) of hexamethyldisiloxane and 6.3 g of methanesulfonic acid were put into the reactor, and 147.6 g of ion-exchanged water was added when it became uniform, and the mixture was stirred at 25° C. for 2 hours. 31.3 g of Kaiwa Chemical Industry Co., Ltd. 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was put in, stirred for 2 hours, and neutralized. Volatile components such as methanol were distilled off under reduced pressure, followed by pressure filtration.

[0127] The obtained reactant was a viscous liquid at 25°C having a viscosity of 2990 mPa·s at 25°C, a volatile content of 2.1% by mass, and a weight average molecular weight of 1770. The values ​​of a to g in the average formula (IV) calculated from the results of NMR were a=0.26, b=0.09, c=0, d=0.10, e=0, f...

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Abstract

The present invention provides an organopolysiloxane that provides an alkali-developable cured film that satisfies both hardness and toughness, and an active energy ray-curable composition containing the organopolysiloxane that can be used as a negative resist material . An organopolysiloxane compound having structural units represented by the following formulae (I) and (II). (where, R 1 and R 5 independently of each other represent a hydrogen atom, methyl, ethyl, n-propyl or isopropyl, R 2 , R 3 and R 6 independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms, R 4 represents a hydrogen atom or a methyl 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 moiety and an active energy ray-curable composition containing the same. Background technique [0002] With the high integration and high speed of LSI, miniaturization of the resist pattern in the manufacturing process of the semiconductor device is required. In addition, in the production of flexible devices represented by organic EL, resist materials having bending resistance and toughness are required. [0003] In general, as a resist pattern, a positive photoresist whose solubility in an alkaline developing solution is increased by exposing it to light is often used. However, a positive photoresist has the following problems: Naphthoquinonediazide sulfonic acid used as a photosensitizer generates sulfonic acid and corrodes metal wiring par...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G77/26G03F7/038
CPCC07F7/0838C08G77/26C08G77/14C08F2/48G03F7/0755
Inventor 藤本卓也吉川裕司
Owner SHIN ETSU CHEM IND CO LTD
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