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Homoadamantane derivatives, process for preparing same, and photoresist compositions

A photoresist and compound technology, applied in the field of new homoadamantane derivatives, can solve problems such as unsatisfactory results, and achieve the effects of excellent exposure sensitivity, reduced roughness, and reduced defects

Inactive Publication Date: 2013-04-10
OSAKA ORGANIC CHEM INDS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, even these methods have failed to achieve satisfactory results

Method used

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  • Homoadamantane derivatives, process for preparing same, and photoresist compositions
  • Homoadamantane derivatives, process for preparing same, and photoresist compositions
  • Homoadamantane derivatives, process for preparing same, and photoresist compositions

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Embodiment

[0078] Examples and comparative examples are shown below, and the present invention will be described more specifically, but the present invention is not limited to them at all.

[0079] In addition, the measuring method of a physical property is as follows.

[0080] (1) Nuclear magnetic resonance spectroscopy (NMR): Measurement was performed with JNM-ECA500 (manufactured by JEOL Ltd.) using deuterated chloroform as a solvent.

[0081] (2) Gas chromatography-mass spectrometry (GC-MS): Measurement was performed using EI (GCMS-QP2010 manufactured by Shimadzu Corporation).

[0082] (3) Weight average molecular weight (Mw), degree of dispersion (Mw / Mn): Measured in terms of polystyrene using an HLC-8220 GPC system (manufactured by Tosoh Corporation, column = TSGgel G-4000HXL + G-2000HXL).

preparation example 1

[0084] (Synthesis of 4-methylsulfonyloxy-2-adamantanone)

[0085] 599.62 g (3.6 mol) of 4-hydroxy-2-adamantanone and 655 mL (4.7 mol) of triethylamine were dissolved in 2.5 L of tetrahydrofuran (THF). Start to slowly add 310 mL (4.0 mol) of methanesulfonyl chloride dropwise thereto. The heat was removed appropriately, the dropwise addition was completed in about 1.5 hours, and the reaction was further performed for 2 hours. 1L of water was added to the reaction solution, and treated by the usual method, 785.74 g (3.2 mol, yield: 89.2%, GC purity: 99.9%) (wherein, Ms represents methylsulfonyl).

[0086] GC-MS: 244 (M ＋ , 11.3%), 165 (15.3%), 148 (27.4%), 120 (43.7%), 91 (29.2%), 79 (100%).

[0087]

preparation example 2

[0089] (Synthesis of endobicyclo[3,3,1]-6-nonene-3-carboxylic acid 1)

[0090] A mixture of 250.52 g (1.0 mol) of 4-methylsulfonyloxy-2-adamantanone synthesized in Preparation Example 1, 460 mL of ethanol, 500 mL (9.5 mol) of 50% aqueous sodium hydroxide solution, and 1.2 L of water was prepared at reflux temperature After reacting for 2 hours, it was cooled to room temperature. Organic impurities contained in the reaction solution were extracted and removed, and then acidified with concentrated hydrochloric acid to precipitate a white solid. The resulting white solid was filtered, and the obtained white filter residue was dissolved with 1.5 L of THF. After the oil and water are separated, they are treated by the usual method to obtain 501.52 g (3.0 mol, yield: 76.4%, GC Purity: 99.2%).

[0091] GC-MS: 166 (M ＋ , 4.7%), 148 (25.4%), 120 (15.5%), 91 (18.9%), 79 (100%).

[0092]

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Abstract

Compounds represented by formula (I), wherein R1 is hydrogen, halogen, methyl, or trifluoromethyl.

Description

technical field [0001] The present invention relates to a novel homoadamantane derivative, a preparation method thereof, a (meth)acrylic polymer, a positive photoresist composition and a resist pattern forming method. Background technique [0002] In recent years, along with progress in the miniaturization of semiconductor elements, further miniaturization is required in the photolithography process in the production thereof. Various use responses to KrF, ArF or F 2 As a method of forming a fine pattern with a photoresist material irradiated with short-wavelength light such as an excimer laser, a new photoresist material capable of responding to short-wavelength irradiated light such as an excimer laser is desired. [0003] As photoresist materials, many phenolic resin-based materials have been studied in the past, but these materials contain aromatic rings, so they absorb light greatly, and cannot obtain pattern accuracy sufficient to cope with miniaturization. [0004] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/10C08F20/28G03F7/039
CPCC07D313/10C08F220/1811C08F220/283G03F7/004G03F7/0397C08F220/20C07D313/06C08F20/28G03F7/039
Inventor 田中慎司上野山义崇大野英俊河野直弥伊藤克树
Owner OSAKA ORGANIC CHEM INDS
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