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Compound, polymer comprising the same and chemically amplified resist composition comprising the polymer

A polymer, a representative technology, applied in the fields of organic chemistry, optics, patterned photoplate process, etc., can solve problems such as unsatisfactory research results and decreased photosensitive speed

Active Publication Date: 2014-12-10
SK MATERIALS PERFORMANCE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these research results are unsatisfactory in realizing finer semiconductor integrated circuits, and there is a problem that the photospeed (photospeed) decreases

Method used

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  • Compound, polymer comprising the same and chemically amplified resist composition comprising the polymer
  • Compound, polymer comprising the same and chemically amplified resist composition comprising the polymer
  • Compound, polymer comprising the same and chemically amplified resist composition comprising the polymer

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example

[0185] 1) Synthesis of sodium salt of difluorohydroxypropane sulfonate

[0186] In an ice bath, 83 g of ethyl 3,3-difluoro-3-sulfopropionate sodium salt was dissolved in 160 mL of methanol and 1.2 L of tetrahydrofuran (THF), and 44 g of sodium borohydride was slowly added dropwise to the solution . After the dropwise addition was complete, the reaction mixture was taken out from the ice bath and heated to 60°C. The reaction mixture was stirred at this temperature for about 4 hours.

[0187] The reaction mixture thus stirred was quenched with distilled water, and then the solvent was removed. The reaction mixture obtained after removing the solvent was redissolved in distilled water, and the obtained solution was acidified to pH 5-6 with concentrated hydrochloric acid.

[0188] The acidified reaction mixture was concentrated again, and methanol was added thereto to obtain a slurry. The slurry was filtered to remove inorganic salts, and the filtrate was washed twice with hex...

Embodiment 1

[0210]As polymerized monomers, 13 g of 2-methyl-2-adamantyl acrylate, 8.4 g of γ-butyrolactone methacrylate, 11.6 g of 3-hydroxy-1-adamantyl methacrylate and 1 g 2-Methacrylic acid-2,2-difluoro-2-sulfopropyl ester diphenyltolylsulfonium salt represented by the formula [D] in the above Reaction Scheme 3 was dissolved in 58 g of 1,2-dichloroethane In order to prepare the monomer mixture.

[0211] A reaction bath was obtained by adding 3.7 g of norbornene, 2.5 g of azobisisobutyronitrile (AIBN) as a polymerization initiator, and 117 g of 1,2-dichloroethane as a polymerization solvent into a 250-mL flask, And nitrogen gas was introduced into the reaction bath. The mixture was stirred for 1 hour while maintaining the temperature at 15°C to 25°C.

[0212] While keeping the temperature of the reaction bath at 65° C., slowly drop the above monomer mixture into the reaction bath within 1 hour to prepare a reaction mixture, and allow the reaction mixture to react for 16 hours. After ...

Embodiment 2

[0217] Polymers were prepared in the same manner as in Example 1 except that the values ​​of l, m, n, o and p in formula (11) were changed by adjusting the amount of each monomer used for polymerization. The l, m, n, o, and p values ​​of the polymer in formula (11) of Example 2 were 0.24 for l, 0.25 for m, 0.30 for n, 0.18 for o, and 0.03 for p.

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Abstract

The invention provides a compound, a polymer comprising the same and a chemically amplified resist composition comprising the polymer. The invention also provides a compound represented by the following formula (1) and a polymer containing the compound as monomer. In the formula (1), definitions of R11, Q1, Q2 and A+ are described in the specification. When the compound and the polymer containing the compound as monomer are applied to chemically amplified resist compositions, such resist compositions achieve excellent sensitivity and relatively high stability, emit less gas and also have relatively high resolution and relatively low line edge roughness.

Description

technical field [0001] The present invention relates to a novel compound, a polymer containing the compound, and a chemically amplified resist composition containing the polymer, in which the compound and a polymer produced by polymerizing the compound as a monomer are used. material, thereby allowing the composition to disperse uniformly and making the composition suitable for forming fine patterns, the composition has characteristics such as high adhesion, high sensitivity and high thermal stability and a reduced amount of gas generation, and can improve resolution and Line edge roughness. More specifically, the present invention relates to a novel compound useful for the preparation of resists capable of being patterned by employing various radiations, such as far-infrared radiation of KrF excimer laser or ArF excimer laser, etc., X-rays such as Synchrotron radiation and charged particle radiation such as electron beams, and thus are suitable for microprocessing; polymers ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/68C07C381/12C07C303/32C08F220/38C08F220/32C08F220/18C08F232/08C08F220/28G03F7/004G03F7/00
CPCC08F20/38G03F7/004G03F7/0045G03F7/0046G03F7/039G03F7/0392
Inventor 朱炫相韩俊熙李承宰金惠渊
Owner SK MATERIALS PERFORMANCE CO LTD
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