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Radiation-sensitive composition and 1, 2-naphthoquinone-2-diazidesulfonic acid derivatives

A radiation-sensitive composition technology, applied in the field of radiation-sensitive composition and 1,2-naphthoquinone-2-diazidesulfonic acid derivatives, can solve the problems of insufficient radiation sensitivity and achieve excellent radiation Effects of Sensitivity and Resolution, Excellent Voltage Hold Characteristics

Pending Publication Date: 2019-10-22
JSR CORPORATIOON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, known 1,2-naphthoquinone-2-diazidesulfonic acid derivatives have problems such as insufficient irradiation sensitivity

Method used

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  • Radiation-sensitive composition and 1, 2-naphthoquinone-2-diazidesulfonic acid derivatives
  • Radiation-sensitive composition and 1, 2-naphthoquinone-2-diazidesulfonic acid derivatives
  • Radiation-sensitive composition and 1, 2-naphthoquinone-2-diazidesulfonic acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0138] Hereinafter, the present invention will be described more specifically based on examples. However, the present invention is not limited to the following examples. In the following description, unless otherwise specified, "parts by mass" are described as "parts".

[0139]

[0140] For the polymer (A), Mw and Mn were measured by gel permeation chromatography (GPC) under the following conditions. In addition, the molecular weight distribution (Mw / Mn) was calculated from the obtained Mw and Mn.

[0141] Device "GPC-101" (manufactured by Showa Denko Co., Ltd.)

[0142] GPC column: bonded GPC-KF-801, GPC-KF-802, GPC-KF-803, and GPC-KF-804 (manufactured by Shimadzu GLC)

[0143] Mobile phase: tetrahydrofuran

[0144] Column temperature: 40°C

[0145] Flow rate: 1.0mL / min

[0146] Sample concentration: 1.0% by mass

[0147] Sample injection volume: 100μL

[0148] Detector: Differential refractometer

[0149] Standard material: monodisperse polystyrene

[0150] 〔...

Synthetic example 1

[0152] 7 parts of 2,2'-azobis(2,4-dimethylvaleronitrile), 200 parts of propylene glycol monomethyl ether acetate, 13 parts of methacrylic acid, 40 parts of glycidyl methacrylate, 10 parts of α-methyl-p-hydroxystyrene, 15 parts of N-cyclohexylmaleimide, 12 parts of tetrahydrofurfuryl methacrylate and 10 parts of n-lauryl methacrylate parts, and 3 parts of α-methylstyrene dimer as a molecular weight modifier, slowly start stirring after nitrogen substitution. After raising the reaction solution to 60° C., the temperature was maintained for 5 hours to obtain a polymer solution containing a copolymer (A-1). The copolymer (A-1) was deposited and precipitated using 900 parts of hexane to the obtained polymer solution. The copolymer (A-1) was separated from the liquid in which the copolymer (A-1) was precipitated, and propylene glycol monomethyl ether acetate was added to the copolymer (A-1) to obtain a copolymer containing 30% by mass of the solid content concentration. The polyme...

Synthetic example 2

[0155] The synthesis scheme of Synthesis Example 2 is shown below.

[0156]

[0157]In a flask equipped with a cooling tube and a stirrer, 0.187 g (0.1 mol) of 6-amino-2-naphthoic acid (A1938 of Tokyo Chemical Industry Co., Ltd.) was dissolved in 100 g of propylene glycol monomethyl ether acetate, and 50 g of After water, 233.0 g of chlorosulfonic acid and 335.7 g of 1,1,2,2-tetrachloroethane were mixed, stirred at 20° C. for 1 week, and the water layer was removed for column separation to obtain compound (b-1 ).

[0158] The obtained compound (b-1) was stirred in 100 g of concentrated sulfuric acid at 400°C for 72 hours, the obtained reaction liquid was added dropwise to water, and the precipitate was filtered to obtain the compound (b-1').

[0159] 0.347g (0.1mol) of compound (b-1') was dispersed and dissolved in 150g of water, 10g of concentrated hydrochloric acid was added, 23.5g of 30% sodium nitrite aqueous solution was added dropwise at about 10°C for 1 hour, and tw...

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Abstract

The invention provides a radiation-sensitive composition having excellent radiation sensitivity and resolution and capable of exhibiting high voltage holding characteristics. The radiation-sensitive composition contains an alkali-soluble polymer (A) and a compound (B) having at least one kinds of structures (bb) selected from a structure represented by Formula (b1) and a structure represented by Formula (b2). In the Formulas (b1) and (b2), X represents an electron-withdrawing group or a halogen atom. When there are a plurality of X, each of them may be the same or different, n1 is an integer of 0 to 3, n2 is an integer of 0 to 2, n1+n2 is an integer of 1 or more, n3 is an integer of 0 to 4, n4 is an integer of 0 to 1, n3+n4 is an integer of 1 or more, and * is a binding site.

Description

technical field [0001] The present invention relates to radiation-sensitive compositions and 1,2-naphthoquinone-2-diazidesulfonic acid derivatives. Background technique [0002] Conventionally, 1,2-naphthoquinone-2-diazidesulfonic acid derivatives have been used as radiation-sensitive compounds in radiation-sensitive compositions (for example, refer to Patent Documents 1 to 3). However, the known 1,2-naphthoquinone-2-diazidesulfonic acid derivatives have problems such as insufficient irradiation sensitivity. [0003] prior art literature [0004] patent documents [0005] Patent Document 1: Japanese Patent Laid-Open No. 2002-088052 [0006] Patent Document 2: Japanese Patent Laid-Open No. 2007-156243 [0007] Patent Document 3: Japanese Patent Laid-Open No. 2006-209113 Contents of the invention [0008] An object of the present invention is to provide a radiation-sensitive composition and a 1,2-naphthoquinone-2-diazidesulfonic acid derivative that have excellent radia...

Claims

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Application Information

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IPC IPC(8): G03F7/004G03F7/008C07C315/00C07C317/44
CPCG03F7/004G03F7/008C07C317/44G03F7/022G03F7/20G03F7/26G03F7/40C07C317/34
Inventor 三村时生角田裕志仓田亮平工藤和生
Owner JSR CORPORATIOON
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