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Silphenylene-containing photocurable composition, pattern formation method using same, and optical semiconductor element obtained using the method

a technology of photocurable composition and silphenylene, which is applied in the direction of photomechanical equipment, instruments, photosensitive materials, etc., can solve the problems of gas emission and discoloration of devices using a stronger light intensity, the inability of resins to undergo the inability to achieve microfabrication in the order of 10 m, etc., to achieve excellent transparency

Inactive Publication Date: 2011-12-22
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006]The present invention has been developed in light of the above circumstances, and has an object of providing a silphenylene-containing photocurable composition that is capable of very fine pattern formation across a broad range of wavelengths, and following pattern formation, yields a film that exhibits a high degree of transparency and superior light resistance, as well as providing a pattern formation method that uses the silphenylene-containing photocurable composition, and an optical semiconductor element that is obtained using the pattern formation method.
[0020]By using the photocurable composition of the present invention comprising a specific alicyclic epoxy-modified silphenylene compound, exposure can be performed with light across a broad range of wavelengths, and thin films can be formed readily with no oxygen inhibition. Further, very fine patterns of 10 μm or less can be formed, and the cured films obtained from the composition exhibit excellent transparency, light resistance and heat resistance, meaning they can be used favorably for protecting and encapsulating optical devices and the like.

Problems solved by technology

However, these resins are not capable of undergoing microfabrication in the order of 10 μm.
When this type of microfabrication is required, resist materials typified by epoxy resin-based materials have often been used, but these resist materials tend to have inadequate light resistance, meaning although there may be no problems with devices of low light intensity, devices that use a stronger light intensity have tended to suffer from problems such as gas emission and discoloration.[Patent Document 1] EP 0 447 926 A2

Method used

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  • Silphenylene-containing photocurable composition, pattern formation method using same, and optical semiconductor element obtained using the method
  • Silphenylene-containing photocurable composition, pattern formation method using same, and optical semiconductor element obtained using the method
  • Silphenylene-containing photocurable composition, pattern formation method using same, and optical semiconductor element obtained using the method

Examples

Experimental program
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Effect test

synthesis example 1

[0077]A flask fitted with a stirrer and a thermometer was charged with 49.7 g (0.4 mols) of 1,2-epoxy-4-vinylcyclohexane, 500 g of toluene and 0.5 g of a 2% by mass ethanol solution of chloroplatinic acid, and with the flask contents undergoing constant stirring, the flask was heated using an oil bath until the internal temperature reached 70° C. Subsequently, 38.9 g (0.2 mols) of 1,4-bis(dimethylsilyl)benzene was added dropwise to the flask over a period of 20 minutes. Following completion of the dropwise addition, the reaction mixture was stirred for 3 hours at 90° C. Following completion of the reaction, the reaction liquid was subjected to a distillation treatment under heating and reduced pressure (50° C., 1 mmHg) using a rotary evaporator until no further distillate was produced, thus yielding 85 g of a silphenylene (A-1) having both terminals modified with alicyclic epoxy groups that represents the component (A).

synthesis example 2

[0078]A flask fitted with a stirrer and a thermometer was charged with 49.7 g (0.4 mols) of 1,2-epoxy-4-vinylcyclohexane, 500 g of toluene and 0.5 g of a 2% by mass ethanol solution of chloroplatinic acid, and with the flask contents undergoing constant stirring, the flask was heated using an oil bath until the internal temperature reached 70° C. Subsequently, 65.1 g (0.1 mols) of an organosiloxane having an average structure represented by formula (7) shown below was added dropwise to the flask over a period of 20 minutes. Following completion of the dropwise addition, the reaction mixture was stirred for 3 hours at 90° C. Following completion of the reaction, the reaction liquid was subjected to a distillation treatment under heating and reduced pressure (50° C., 1 mmHg) using a rotary evaporator until no further distillate was produced, thus yielding 110 g of an epoxy-modified siloxane compound (B-1) having an average structure represented by formula (8) shown below.

synthesis example 3

[0079]A flask fitted with a stirrer and a thermometer was charged with 27.3 g (0.22 mols) of 1,2-epoxy-4-vinylcyclohexane, 16.8 g (0.09 mols) of 1,3-divinyl-1,1,3,3-tetramethylpropanedisiloxane, 500 g of toluene and 0.5 g of a 2% by mass ethanol solution of chloroplatinic acid, and with the flask contents undergoing constant stirring, the flask was heated using an oil bath until the internal temperature reached 70° C. Subsequently, 24.1 g (0.1 mols) of 1,3,5,7-tetramethylcyclotetrasiloxane was added dropwise to the flask over a period of 20 minutes. Following completion of the dropwise addition, the reaction mixture was stirred for 3 hours at 90° C. Following completion of the reaction, the reaction liquid was subjected to a distillation treatment under heating and reduced pressure (50° C., 1 mmHg) using a rotary evaporator until no further distillate was produced, thus yielding 65 g of an epoxy-modified siloxane compound (B-2) having an average structure represented by formula (9) ...

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Abstract

Provided is a silphenylene-containing photocurable composition including: (A) a specific silphenylene having both terminals modified with alicyclic epoxy groups, and (C) a photoacid generator that generates acid upon irradiation with light having a wavelength of 240 to 500 nm. Also provided is a pattern formation method including: (i) forming a film of the photocurable composition on a substrate, (ii) exposing the film through a photomask with light having a wavelength of 240 to 500 nm, and if necessary, performing heating following the exposure, and (iii) developing the film in a developing liquid, and if necessary, performing post-curing at a temperature within a range from 120 to 300° C. following the developing. Further provided is an optical semiconductor element obtained by performing pattern formation using the method. The composition is capable of very fine pattern formation across a broad range of wavelengths, and following pattern formation, yields a film that exhibits a high degree of transparency and superior light resistance. The composition may also include: (B) a specific epoxy group-containing organosilicon compound.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]The present invention relates to a silphenylene-containing photocurable composition, a pattern formation method that uses the composition, and an optical semiconductor element obtained using the method. The invention relates particularly to a silphenylene-containing photocurable composition which, due to its superior properties of transparency, light resistance and heat resistance, is useful in optical devices typified by light-emitting elements such as light-emitting diodes (LED), light-receiving elements such as photodiodes, optical sensors and CMOS image sensors, and optical transmission devices such as optical waveguides, as well as a pattern formation method that uses the silphenylene-containing photocurable composition, and an optical semiconductor element obtained using the method.[0003]2. Description of the Prior Art[0004]Epoxy resins have typically been used as the encapsulating protective material within vario...

Claims

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Application Information

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IPC IPC(8): B32B3/10G03F7/30G03F7/004
CPCC08G59/306C08L63/00C08L2312/06Y10T428/24802G03F7/0755G03F7/0005C08L83/04G03F7/0754H01L21/0274
Inventor TAGAMI, SHOHEISAKURAI, TAKATOKATO, HIDETO
Owner SHIN ETSU CHEM IND CO LTD
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